Recent developments in asymmetric cyclopropanation
TetrahedronPublished 26 April 2008
Hélène Pellissier
Citations562
SJR quartileQ3
SJR score0.43
SNIP0.60
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
This review is intended to update the most recent developments of asymmetric cyclopropanation in numerous reaction types, such as Simmons–Smith cyclopropanations, Michael-initiated ring-closure reactions, transition-metal-catalysed decomposition of diazoalkanes, and miscellaneous reactions, covering the literature from 2003 to 2007. This review clearly demonstrates the diversity and power of asymmetric cyclopropanation in the field of synthetic organic chemistry.
Keywords
Chemistry
Ionic Liquids in Synthesis
3,933 Citations2002
Chemical ReviewsStereoselective Cyclopropanation Reactions
1,783 Citations2003H. Lebel, Jean-François Marcoux +2 more
This review will focus mainly on the new methods that have appeared in the literature since 1989 for stereoselective cyclopropanation reactions from olefins: the halomethylmetal-mediated cycloalkane reactions, the transition metal-catalyzed decomposition of diazo compounds, and the nucleophilic addition-ring closure sequence.
Chemical ReviewsTransition Metal-Mediated Cycloaddition Reactions
1,768 Citations1996Mark Lautens, Wolfgang Klute +1 more
The phytochemical remains of the seven-membered ring formation are still under investigation, but it is clear that the polymethine content of the ring is lower than previously thought, suggesting that it is more likely to be a mixture of 22π and 32σ.
Chemical ReviewsDonor−Acceptor-Substituted Cyclopropane Derivatives and Their Application in Organic Synthesis
1,577 Citations2003Hans‐Ulrich Reißig, Reinhold Zimmer
Chemical ReviewsRecent Advances in Asymmetric Catalytic Metal Carbene Transformations
1,383 Citations1998Michael P. Doyle, David C. Forbes
Chemical ReviewsTransition Metal Chemistry of Cyclopropenes and Cyclopropanes
1,260 Citations2007Michael Rubin, Marina Rubina +1 more
Chemical ReviewsUse of cyclopropanes and their derivatives in organic synthesis
949 Citations1989Henry Ν. C. Wong, Moon Yuen Hon +4 more
Chemical Reviews<i>C</i><sub>2</sub>-Symmetric Chiral Bis(Oxazoline) Ligands in Asymmetric Catalysis
793 Citations2006Giovanni Desimoni, Giuseppe Faita +1 more
Journal of the American Chemical SocietyA New Synthesis of Cyclopropanes<sup>1</sup>
719 Citations1959Howard E. Simmons, Ronald D. Smith
TetrahedronRecent advances in donor–acceptor (DA) cyclopropanes
686 Citations2004Ming Yu, Brian L. Pagenkopf
Chemical ReviewsRecent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis
649 Citations2004Helen A. McManus, Patrick J. Guiry
Journal of the American Chemical SocietyA NEW SYNTHESIS OF CYCLOPROPANES FROM OLEFINS
647 Citations1958Howard E. Simmons, Ronald D. Smith
Chemical ReviewsBiosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds
629 Citations2003Ludger A. Wessjohann, Wolfgang Brandt +1 more
Chemical ReviewsAsymmetric Synthesis of Active Pharmaceutical Ingredients
546 Citations2006Vittorio Farina, Jonathan T. Reeves +2 more
Journal of the American Chemical SocietyPlatinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated Enynes
544 Citations2004Victor Mamane, Tobias Gress +2 more
It is shown that conversion of the hydroxylated enynes into the corresponding acetates followed by reaction with a cationic gold catalyst formed from (PPh3)AuCl and AgSbF6 opens entry into isomeric products bearing the ketone function at the C-2 position of the bicyclo[3.1.0]hexan-3-one derivatives.
Journal of the American Chemical SocietyGold(I)-Catalyzed Stereoselective Olefin Cyclopropanation
528 Citations2005Magnus J. Johansson, David J. Gorin +2 more
This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective preparation of vinyl cyclopropanes with high cis-selectivity.
Chemical Reviews1,<i>n</i>-Dicarbanionic Titanium Intermediates from Monocarbanionic Organometallics and Their Application in Organic Synthesis
425 Citations2000Oleg G. Kulinkovich, Armin de Meijere
Angewandte Chemie International EditionDNA‐Based Asymmetric Catalysis
404 Citations2005Gérard Roelfes, Ben L. Feringa
In this tutorial review, the ideas behind this novel concept of DNA-based asymmetric catalysis are introduced, an overview of the catalytic chemistry available to date will be given and the role of DNA in catalysis will be discussed.
Journal of the American Chemical SocietyEnantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation
371 Citations2005Roxanne K. Kunz, David W. C. MacMillan
This study outlines the identification of a new class of iminium catalyst based on the concept of directed electrostaticactivation (DEA) that exploits dual activation of ylide and enal substrates through a proposed electrostatic activation and stereodirected protocol.
Angewandte Chemie International EditionElectrophilic Activation and Cycloisomerization of Enynes: A New Route to Functional Cyclopropanes
363 Citations2005Christian Bruneau
The recent developments in electrophilic activation of enynes are discussed and it is shown that simple catalysts such as [Ru(3)(CO)(12)], PtCl(2), and cationic gold complexes are efficient precursors to promote the formation of functional polyclic compounds.
Topics in current chemistryCyclopropane Derivatives and their Diverse Biological Activities
357 Citations1999Jacques Salaün
Natural and synthetic cyclopropanes bearing simple functionalities are endowed with a large spectrum of biological properties ranging from enzyme inhibitions to insecticidal, antifungal, herbicidal, antimicrobial, antibiotic, antibacterial, antitumor and antiviral activities.
Chemical ReviewsStructure, Synthesis, and Chemical Reactions of Fluorinated Cyclopropanes and Cyclopropenes
352 Citations2003William R. Dolbier, Merle A. Battiste
Chemical Society ReviewsRuthenium-catalysed carbenoid cyclopropanation reactions with diazo compounds
341 Citations2004Gerhard Maas
In this tutorial review, several different ruthenium complexes are presented which have recently emerged as suitable catalysts for carbenoid cyclopropanation.
Chemical ReviewsSyntheses of<i>gem</i>-Dihalocyclopropanes and Their Use in Organic Synthesis
335 Citations2003Michał Fedoryński
Chemical ReviewsThe Electrophilic Nature of Carbenoids, Nitrenoids, and Oxenoids
328 Citations2001Gernot Boche, John C. W. Lohrenz
Pure and Applied ChemistryCatalytic asymmetric synthesis of cyclopropanecarboxylic acids: an application of chiral copper carbenoid reaction
327 Citations1985Tadatoshi Aratani
Chemical ReviewsSynthesis and Applications of β-Aminocarboxylic Acids Containing a Cyclopropane Ring
309 Citations2003Frieder Gnad, Oliver Reiser
Journal of the American Chemical SocietyCatalytic Enantioselective Hydroboration of Cyclopropenes
306 Citations2003Marina Rubina, Michael Rubin +1 more
2,2-Disubstituted cyclopropyl boronates have been synthesized with high degrees of diastereo- and enantioselectivity via the rhodium-catalyzed asymmetric hydroboration of 3,3-disubstitute cycloprostenes through the Suzuki cross-coupling reaction.
Chemistry - A European JournalPlatinum‐ and Gold‐Catalyzed Rearrangement Reactions of Propargyl Acetates: Total Syntheses of (−)‐α‐Cubebene, (−)‐Cubebol, Sesquicarene and Related Terpenes
285 Citations2006Alois Fürstner, Peter Hannen
The alternative phasing of events, implying initial attack of the acetate (rather than the alkene moiety) onto the metal-alkyne complex, is inconsistent with the stereochemical data obtained during this total synthesis campaign.
Angewandte Chemie International EditionEnantioselective Organocatalytic Cyclopropanation via Ammonium Ylides
275 Citations2004Charles D. Papageorgiou, Maria A. Cubillo de Dios +2 more
Angewandte Chemie International EditionFascinating Natural and Artificial Cyclopropane Architectures
263 Citations2001Rüdiger Faust
Chemical ReviewsSynthesis and Properties of Oligocyclopropyl-Containing Natural Products and Model Compounds
259 Citations2003Jörg Pietruszka
Angewandte Chemie International EditionEnantiomerically Enriched Cyclopropene Derivatives: Versatile Building Blocks in Asymmetric Synthesis
254 Citations2007Ilan Marek, Samah Simaan +1 more
The ready availability of a wide range of enantiomerically enriched methylene- and alkylidenecyclopropane derivatives now provides an excellent opportunity to discover new and unique transformations that can further enrich mainstream synthetic methodology.
Journal of the American Chemical SocietyCobalt-Catalyzed Asymmetric Cyclopropanation of Electron-Deficient Olefins
235 Citations2007Ying Chen, Joshua V. Ruppel +1 more
Journal of the American Chemical SocietyBromoporphyrins as Versatile Synthons for Modular Construction of Chiral Porphyrins: Cobalt-Catalyzed Highly Enantioselective and Diastereoselective Cyclopropanation
224 Citations2004Ying Chen, Kimberly B. Fields +1 more
5,10-Bis(2',6'-dibromophenyl)porphyrins bearing various substituents at the 10 and 20 positions were demonstrated to be versatile synthons for modular construction of chiral porphyrins via palladium-catalyzed amidation reactions with chiral amides.
Helvetica Chimica ActaCatalytic asymmetric synthesis of <i>Secondary</i> (<i>E</i>)‐allyl alcohols from acetylenes and aldehydes <i>via</i> (1‐alkenyl)zinc intermediates. Preliminary Communication
222 Citations1992Wolfgang Oppolzer, Rumen Radinov
Angewandte Chemie International EditionEnantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts
202 Citations2006Carin C. C. Johansson, Nadine Bremeyer +4 more
Current Opinion in Chemical BiologyEnzyme catalysed deracemisation and dynamic kinetic resolution reactions
201 Citations2004Nicholas J. Turner
New catalysts and reaction conditions have been developed for the dynamic kinetic resolution or deracemisation of racemic mixtures of chiral compounds, with a general theme of an enantioselective enzyme with a chemical reagent being used either to racemise the unreactive enantiomer or alternatively recycle an intermediate in the deracema process.
Advanced Synthesis & CatalysisA Simple Organocatalytic Enantioselective Cyclopropanation of α,β‐Unsaturated Aldehydes
196 Citations2007Ramón Rios, Henrik Sundén +4 more
A highly chemo- and enantioselective organocatalytic cyclopropanation of aldehydes with bromomalonate and 2-bromoacetoacetate esters is presented and gives access to 2-formylcyclopropanes in high yields and up to 99?% ee.
Angewandte Chemie International EditionCopper Carbene Complexes: Advanced Catalysts, New Insights
187 Citations2003Wolfgang Kirmse
Although the present report focuses on copper complexes, outstanding results with other metals are also covered, and structural evidence for the transients of catalyzed diazo decomposition is becoming available through experiment and computation.
Angewandte Chemie International EditionOrganic‐Catalyst‐Mediated Cyclopropanation Reaction
185 Citations2003Charles D. Papageorgiou, Steven V. Ley +1 more
Journal of the American Chemical SocietyEnantioselective Synthesis of Vinylcyclopropanes and Vinylepoxides Mediated by Camphor-Derived Sulfur Ylides: Rationale of Enantioselectivity, Scope, and Limitation
185 Citations2006Xianming Deng, Ping Cai +7 more
By a sidearm approach, camphor-derived sulfur ylides 1 were designed and synthesized for the cyclopropanation of electron-deficient alkenes and epoxidation of aldehydes and the sidearmed hydroxyl group was found to play a key role in the control of enantioselectivity and diastereoselectivities.
Journal of the American Chemical SocietyCombined C−H Activation/Cope Rearrangement as a Strategic Reaction in Organic Synthesis: Total Synthesis of (−)-Colombiasin A and (−)-Elisapterosin B
182 Citations2006Huw M. L. Davies, Xing Dai +1 more
The total synthesis of (-)-colombiasin A and (-)-elisapterosin B has been achieved where one enantiomer of the dihydronaphthalene undergoes the combined C-H activation/Cope rearrangement while the other undergoes cyclopropanation.
Angewandte Chemie International EditionAn Intramolecular Organocatalytic Cyclopropanation Reaction
181 Citations2004Nadine Bremeyer, Stephen C. Smith +2 more
The development of a new organocatalytic intramolecular cyclopropanation reaction that forms synthetically versatile bicycloalkanes by using a nucleophilic tertiary amine catalyst is described.
Coordination Chemistry ReviewsCarbohydrate derivative ligands in asymmetric catalysis
177 Citations2004Montserrat Diéguez, Òscar Pàmies +4 more
Journal of the American Chemical SocietyExpedient Synthesis of Cyclopropane α-Amino Acids by the Catalytic Asymmetric Cyclopropanation of Alkenes Using Iodonium Ylides Derived from Methyl Nitroacetate
177 Citations2005Benoît Moreau, André B. Charette
1-Nitrocyclopropyl esters are versatile building blocks to access the corresponding cyclopropane amino esters and aminocyclopropanes in two and three steps, respectively, from commercially available products.
Angewandte Chemie International EditionSynthesis of (−)‐Cubebol by Face‐Selective Platinum‐, Gold‐, or Copper‐Catalyzed Cycloisomerization: Evidence for Chirality Transfer
169 Citations2006Charles Fehr, José Galindo
Accounts of Chemical ResearchAsymmetric Transfer of Carbenes with Phenyliodonium Ylides
169 Citations2004Paul Müller
Phenyliodonium ylides react in the presence of rhodium(II) or copper catalysts to afford products derived from carbenoid pathways, indicating metallocarbene intermediates with both precursors.
The Journal of Organic ChemistryA Novel Class of Tunable Zinc Reagents (RXZnCH<sub>2</sub>Y) for Efficient Cyclopropanation of Olefins
165 Citations2003Jon C. Lorenz, Jiang Long +4 more
A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopromation of uncoupled oleFins.
The Journal of Organic ChemistryDiastereoselective and Enantioselective Cyclopropanation of Alkenes Catalyzed by Cobalt Porphyrins
149 Citations2003Lingyu Huang, Ying Chen +2 more
Cobalt(II) porphyrin complexes were shown to be general and efficient catalysts for selective cyclopropanation of alkenes with ethyl diazoacetate (EDA) without the need of slow addition of EDA.
Coordination Chemistry ReviewsOptically active ruthenium porphyrins: chiral recognition and asymmetric catalysis
146 Citations2002Gérard Simonneaux, Paul Le Maux
The Journal of Organic ChemistryAsymmetric Cyclopropanation of Styrenes Catalyzed by Metal Complexes of <i>D</i><sub>2</sub>-Symmetrical Chiral Porphyrin: Superiority of Cobalt over Iron
142 Citations2007Ying Chen, X. Peter Zhang
The high catalytic activity and selectivity of [Co(1)] evidently resulted from the appropriate combination of the cobalt ion and the chiral porphyrin 1 as the use of iron(III) complex of the same ligand [Fe(1)Cl] afforded the desired cyclopropane products in low yields and poor enantioselectivity.
Topics in current chemistryBicyclopropylidene — A Unique Tetrasubstituted Alkene and a Versatile C6-Building Block
142 Citations1999Armin de Meijere, S.I. Kozhushkov +1 more
The Journal of Organic ChemistrySynthesis of New Chiral 2,2‘-Bipyridine Ligands and Their Application in Copper-Catalyzed Asymmetric Allylic Oxidation and Cyclopropanation
139 Citations2003Andrei V. Malkov, Daniele Pernazza +6 more
Copper(I) complexes derived from bipyridine-type ligands and (TfO)(2)Cu (1 mol %) upon an in situ reduction with phenylhydrazine exhibit good enantioselectivity and unusually high reaction rate in allylic oxidation of cyclic olefins.
Organic LettersCatalytic Cyclopropanation of Alkenes Using Diazo Compounds Generated in Situ. A Novel Route to 2-Arylcyclopropylamines
139 Citations2001Varinder K. Aggarwal, Javier de Vicente +1 more
A user-friendly, one-pot process for catalytic cyclopropanation of alkenes from tosylhydrazones is described, and this is exemplified in the efficient synthesis of the HIV-1 reverse transcriptase inhibitor 6.
Journal of the American Chemical SocietyAsymmetric Catalysis on the Intramolecular Cyclopropanation of α-Diazo-β-keto Sulfones
138 Citations2003Masahiro Honma, Takashi Sawada +8 more
The development of a highly enantioselective asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones, which possesses great potential for natural product synthesis because many different chemistries ofcyclopropane, ketone, and sulfone are available.
The Journal of Organic ChemistryStereoselective Synthesis of Highly Functionalized Nitrocyclopropanes via Organocatalyic Conjugate Addition to Nitroalkenes
130 Citations2006Séamus H. McCooey, Thomas McCabe +1 more
A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported.
Organic LettersEnantioselective Synthesis of Trifluoromethyl-Substituted Cyclopropanes
130 Citations2007Justin R. Denton, Dinesh K. Sukumaran +1 more
SynthesisSelectivity in Rhodium(II)Catalyzed Reactions of Diazo Compounds: Effects of Catalyst Electrophilicity,Diazo Substitution, and Substrate Substitution. From Chemoselectivityto Enantioselectivity
125 Citations2003Craig A. Merlic, Andrea L. Zechman
Coordination Chemistry ReviewsRuthenium and osmium porphyrin carbene complexes: synthesis, structure, and connection to the metal-mediated cyclopropanation of alkenes
120 Citations2002Chi‐Ming Che, Jie‐Sheng Huang
Journal of the American Chemical SocietyControllable Diastereoselective Cyclopropanation. Enantioselective Synthesis of Vinylcyclopropanes via Chiral Telluronium Ylides
120 Citations2003Wei‐Wei Liao, Kai Li +1 more
Either one of the two diastereomers could be enantioselectively synthesized at will just by the choice of LiTMP/HMPA or LDA/LiBr.
Angewandte Chemie International EditionEnantioselective Synthesis of Complementary Double‐Helical Molecules that Catalyze Asymmetric Reactions
119 Citations2007Takashi Hasegawa, Yoshio Furusho +2 more
SynthesisCatalytic Enantioselective Cyclopropanation of Olefins Using Carbenoid Chemistry
115 Citations1997Vinod K. Singh, Arpita DattaGupta +1 more
Tetrahedron AsymmetryRhodium(II)-catalyzed olefin cyclopropanation with the phenyliodonium ylide derived from Meldrum's acid
115 Citations2003Paul Müller, Yves Allenbach +1 more
Journal of the American Chemical SocietyIodomethylzinc Phosphates: Powerful Reagents for the Cyclopropanation of Alkenes
111 Citations2005Marie‐Christine Lacasse, Cyril Poulard +1 more
A new family of zinc carbenoids derived from phosphoric acids was developed and used in the cyclopropanation of allylic alcohols and ethers and also of unfunctionalized olefins.
SynlettThe Asymmetric Cyclopropanation of Acyclic Allylic Alcohols: Efficient Stereocontrol with Iodomethylzinc Reagents
107 Citations1995André B. Charette, Jean-François Marcoux
The Journal of Organic ChemistryTetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst
106 Citations2007Antti Hartikka, Per I. Arvidsson
The improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.
Journal of the American Chemical SocietyCatalytic Enantioselective Hydrostannation of Cyclopropenes
105 Citations2004Marina Rubina, Michael Rubin +1 more
The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated and allows for the efficient synthesis of 2,2-disubstitutedcyclopropylstannanes with high degrees of diastereo- and enantiOSElectivity.
Angewandte Chemie International EditionEnantioselective Synthesis of Arglabin
103 Citations2007K. Srinivas, Won Boo Jeong +4 more
Journal of Organometallic ChemistryTitanium-mediated syntheses of cyclopropylamines
102 Citations2004Armin de Meijere, S.I. Kozhushkov +1 more
Journal of the American Chemical SocietyEnantioselective, Facially Selective Carbomagnesation of Cyclopropenes
101 Citations2006Xiaozhong Liu, Joseph M. Fox
The facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products.
Journal of the American Chemical SocietySimple Strategy for the Immobilization of Dirhodium Tetraprolinate Catalysts Using a Pyridine-Linked Solid Support
99 Citations2004Huw M. L. Davies, Abbas M. Walji +1 more
Three-phase test studies indicated that a very slow reaction occurs when both the catalyst and the diazo compound were immobilized, but the slow rate precluded the likelihood that the cyclopropanation was predominately occurring by a release-and-capture mechanism.
Organic LettersUniversal Strategy for the Immobilization of Chiral Dirhodium Catalysts
97 Citations2005Huw M. L. Davies, Abbas M. Walji
Chiral rhodium(II) catalysts used in asymmetric carbenoid chemistry can be efficiently heterogenized using a novel immobilization strategy and can be effectively recycled with limited loss in stereoselectivity.
The Journal of Organic ChemistryVitamin B<sub>12</sub> Derivatives as Natural Asymmetric Catalysts: Enantioselective Cyclopropanation of Alkenes
95 Citations2004Ying Chen, X. Peter Zhang
Reactivity studies under different conditions suggest that the active species in the proposed catalytic cycle is the base-on cob(II)alamin (B(12r)) that is generated possibly via in situ reduction of B(12a) by EDA.
Organic LettersCatalytic Asymmetric Simmons−Smith Cyclopropanation of Silyl Enol Ethers. Efficient Synthesis of Optically Active Cyclopropanol Derivatives
94 Citations2006Haifeng Du, Jiang Long +1 more
A catalytic asymmetric Simmons-Smith cyclopropanation of silyl enol ethers using dipeptide 2 as the ligand and up to 96% ee was obtained.
TetrahedronIridium-catalyzed enantioselective cycloisomerization of nitrogen-bridged 1,6-enynes to 3-azabicylo[4.1.0]heptenes
93 Citations2005Takanori Shibata, Yuka Kobayashi +3 more
Chemistry - A European JournalElectronically Tuned Chiral Ruthenium Porphyrins: Extremely Stable and Selective Catalysts for Asymmetric Epoxidation and Cyclopropanation
92 Citations2003Albrecht Berkessel, Patrick Kaiser +1 more
Three enantiomerically pure and electronically tuned ruthenium carbonyl porphyrin catalysts for the asymmetric cyclopropanation and epoxidation of a variety of olefinic substrates are reported.
Journal of the American Chemical SocietyAsymmetric Simmons−Smith Cyclopropanation of Unfunctionalized Olefins
92 Citations2003Jiang Long, Yi Yuan +1 more
This paper describes a promising asymmetric cyclopropanation system for unfunctionalized olefins using readily available dipeptide N-Boc-l-Val- l-Pro-OMe as ligand.
The Journal of Organic ChemistrySynthesis of (1<i>R</i>,2<i>S</i>)-1-Amino-2-vinylcyclopropanecarboxylic Acid Vinyl-ACCA) Derivatives: Key Intermediates for the Preparation of Inhibitors of the Hepatitis C Virus NS3 Protease
88 Citations2005Pierre L. Beaulieu, James Gillard +12 more
Chemistry - A European JournalAsymmetric Sulfonium Ylide Mediated Cyclopropanation: Stereocontrolled Synthesis of (+)‐LY354740
86 Citations2005Varinder K. Aggarwal, Emma Grange
The model for selectivity has been applied to other sulfonium ylide mediated cyclopropanation reactions and successfully accounts for the diastereoselectivity observed in all such reported reactions to date.
Journal of the American Chemical SocietyHighly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl Alcohols with up to Four Contiguous Stereocenters
86 Citations2005Hun Young Kim, Alice E. Lurain +3 more
Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropy alcohols with up to four contiguous stereocenters are reported.
Journal of the American Chemical SocietyIntramolecular Cyclopropanation of Unsaturated Terminal Epoxides and Chlorohydrins
86 Citations2007David M. Hodgson, Ying Kit Chung +5 more
Lithium 2,2,6,6-tetramethylpiperidide (LTMP)induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ol and other bicyclic adducts.
Journal of the American Chemical SocietyThe Michael Addition−Elimination of Ylides to α,β-Unsaturated Imines. Highly Stereoselective Synthesis of Vinylcyclopropanecarbaldehydes and Vinylcyclopropylaziridines
86 Citations2005Jun‐Cheng Zheng, Wei‐Wei Liao +3 more
The Michael addition−elimination of ylide to α,β-unsaturated imines leads to a highly diastereoselective and enantioselectives synthesis of vinylcyclopropanecarbaldehydes in good to high yields for the first time.
Chemical CommunicationsA new asymmetric organocatalytic nitrocyclopropanation reaction
85 Citations2006Henriette M. Hansen, Deborah A. Longbottom +1 more
Using 5-(pyrrolidin-2-yl)-1H-tetrazole as an organic catalyst, the nitrocyclopropanation of 2-cyclohexen-1-one has been achieved, proceeding in high yield and with good enantioselective control.
Organic LettersDirhodium Tetraprolinate-Catalyzed Asymmetric Cyclopropanations with High Turnover Numbers
84 Citations2003Huw M. L. Davies, Chandrasekar Venkataramani
The bridged dirhodium tetraprolinate Rh(2)(S-biTISP)(2) (2) catalyzes the asymmetric cyclopropanation reaction between methyl phenyldiazoacetate and styrene at room temperature with high turnover number and turnover frequency.
Angewandte Chemie International EditionConstruction of an Aryliridium–Salen Complex for Highly <i>cis</i>‐ and Enantioselective Cyclopropanations
82 Citations2007Shigefumi Kanchiku, Hidehiro Suematsu +3 more
Organic LettersFacile Asymmetric Synthesis of the Core Nuclei of Xanthanolides, Guaianolides, and Eudesmanolides
82 Citations2003Bernd Nosse, Rakeshwar B. Chhor +3 more
Key steps were a copper(I)-catalyzed asymmetric cyclopropanation, Sakurai allylations, intramolecular ene reactions, and ring-closing metathesis reactions.
Journal of the American Chemical SocietySynthesis of the Polycyclopropane Antibiotic FR-900848 via the Horeau Gambit
82 Citations1996John R. Falck, Belew Mekonnen +2 more
Chemistry - A European JournalSupported Ionic‐Liquid Films (SILF) as Two‐Dimensional Nanoreactors for Enantioselective Reactions: Surface‐Mediated Selectivity Modulation (SMSM)
81 Citations2006M. Rosa Castillo, Leslie Fousse +3 more
Only layered solids with negative charges in the layers (clays) give rise to this type of behaviour, showing that the formation of ion pairs may be a decisive factor and also shows the existence of differences between bulk and supported ionic liquids.
Organic LettersTotal Synthesis of the Marine Natural Product (−)-Clavosolide A. A Showcase for the Petasis−Ferrier Union/Rearrangement Tactic
80 Citations2006Amos B. Smith, Vladimir Simov
The total synthesis of the marine diolide (-)-clavosolide A has been achieved in 17 steps (longest linear sequence) from commercially available crotonaldehyde exploiting the Petasis-Ferrier union/rearrangement tactic to construct the requisite aglycon monomer.
Chemistry - A European JournalUnprecedented Stereoselective Synthesis of Catalytically Active Chiral Mo<sub>3</sub>CuS<sub>4</sub> Clusters
79 Citations2005M. Feliz, Eva Guillamón +5 more
Organic LettersSelectivity Enhancement in the Rh(II)-Catalyzed Cyclopropanation of Styrene with (Silanyloxyvinyl)diazoacetates
79 Citations2004Paul Müller, Gérald Bernardinelli +3 more
Journal of the American Chemical SocietyTotal Synthesis of the Pentacyclopropane Antifungal Agent FR-900848
79 Citations1996Anthony G. M. Barrett, Krista Kasdorf
Organic LettersRh(II)-Catalyzed Enantioselective Cyclopropanation of Olefins with Dimethyl Malonate via in Situ Generated Phenyliodonium Ylide
79 Citations2004Paul Müller, Ashraf Ghanem
Olefins are cyclopropanated with dimethyl malonate (1a) iodosylbenzene (PhI=O) and a Rh(II) carboxylate catalyst via an in situ generated phenyliodonium ylide (1c) and enantioselectivities of up to 90% for 4-bromostyrene and 98% for pent-1-ene have been observed.
Tetrahedron AsymmetryNew bis(oxazoline) ligands with secondary binding sites for the asymmetric cyclopropanation of furans
78 Citations2003Marina Schinnerl, Claudius Böhm +2 more
Journal of the American Chemical SocietyVinyldiazolactone as a Vinylcarbene Precursor: Highly Selective C−H Insertion and Cyclopropanation Reactions
77 Citations2006Darren Bykowski, Kou-Hui Wu +1 more
The vinyldiazolactone precursor to the metal vinylcarbene possesses superior stability in comparison to previously known vinyLDiazoacetates and, for the first time, allows the use of Z-vinylcarbenes in asymmetric C-H insertion and cyclopropanation reactions.
…