An efficient organocatalytic enantioselective synthesis of spironitrocyclopropanes
Organic & Biomolecular ChemistryPublished 22 October 2012
Utpal Das, Yi-Ling Tsai, Wenwei Lin
Citations53
SJR quartileQ2
SJR score0.60
SNIP0.71
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.
TL;DR
An organocatalytic asymmetric synthesis of spironitrocyclopropanes has been demonstrated starting from 2-arylidene-1,3-indandiones and bromonitroalkanes catalyzed by a cinchona-derived bifunctional organoc atalyst.
Abstract
An organocatalytic asymmetric synthesis of spironitrocyclopropanes has been demonstrated starting from 2-arylidene-1,3-indandiones and bromonitroalkanes catalyzed by a cinchona-derived bifunctional organocatalyst. The products were obtained with excellent enantioselectivities, diastereoselectivities and with good yields.
Keywords
Chemistry
Chemical ReviewsSmall-Molecule H-Bond Donors in Asymmetric Catalysis
2,574 Citations2007Abigail G. Doyle, Eric N. Jacobsen
Angewandte Chemie International EditionAsymmetric Catalysis by Chiral Hydrogen‐Bond Donors
1,900 Citations2006Mark S. Taylor, Eric N. Jacobsen
This review documents the structural and mechanistic features that contribute to high enantioselectivity in hydrogen-bond-mediated catalytic processes in small-molecule, synthetic catalyst systems.
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.
Advanced Synthesis & CatalysisRecent Progress in Chiral Brønsted Acid Catalysis
888 Citations2006Takahiko Akiyama, Junji Itoh +1 more
Chemical CommunicationsAsymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
815 Citations2008Stephen J. Connon
Cinchona alkaloid derivatives modified to include a (thio)urea component have emerged in the last three years as readily accessible, robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations.
Chemical CommunicationsEnantioselective synthesis of all-carbon quaternary stereogenic centers in acyclic systems
677 Citations2011Jaya Prakash Das, Ilan Marek
This feature article summarizes the methods for the creation of all-carbon quaternary stereogenic centers in acyclic systems and is divided into sections on substitution and additions reactions, alkylation, aldol, Mannich and rearrangements reactions.
Chemistry - An Asian JournalHydrogen‐Bond‐Mediated Asymmetric Catalysis
621 Citations2008Xinhong Yu, Wei Wang
The examples provided neatly demonstrate that chiral ureas and thioureas, diols, and phosphoric acids display effective and unique activation modes of catalysis for a broad spectrum of asymmetric organic transformations, including single-step and multiple-step cascade reactions.
TetrahedronSynthesis of cyclopropane containing natural products
615 Citations2001William A. Donaldson
Chemical Society ReviewsRecent advances in the total synthesis of cyclopropane-containing natural products
576 Citations2012David Y.‐K. Chen, Rebecca H. Pouwer +1 more
The examples showcased herein aim to inspire students and practitioners of organic synthesis to seek further advances in the chemical synthesis of cyclopropane-containing natural products, both in the context of target-oriented syntheses and method developments.
SynthesisOrganocatalytic Formation of Quaternary Stereocenters
548 Citations2009Marco Bella, Tecla Gasperi
Chemical CommunicationsMetal-catalyzed asymmetric conjugate addition reaction: formation of quaternary stereocenters
467 Citations2010Christine Hawner, Alexandre Alexakis
Different ways of activating the conjugate system towards nucleophilic addition will be described, and an overview will be given on the different types of quaternary centers that are accessible through the Conjugate addition reaction.
Angewandte Chemie International EditionApplication of Chiral Sulfides to Catalytic Asymmetric Aziridination and Cyclopropanation with In Situ Generation of the Diazo Compound
375 Citations2001Varinder K. Aggarwal, Emma Alonso +4 more
The PTC-Ts=phase-transfer catalyst process is particularly suited to the synthesis of conformationally locked cyclopropyl amino acids, which can now be prepared in only three steps from commercially available material in 100 % ee.
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.
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.
Journal of the American Chemical SocietyOrganocatalytic Enantioselective Cascade Michael-Alkylation Reactions: Synthesis of Chiral Cyclopropanes and Investigation of Unexpected Organocatalyzed Stereoselective Ring Opening of Cyclopropanes
344 Citations2007Hexin Xie, Liansuo Zu +3 more
This investigation represents the first example of an organocatalyst-promoted ring opening of the cyclopropanes, whereas such reactions have been intensively explored by Lewis acid-based catalysis.
Journal of the American Chemical SocietyRhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with<i>N</i>-Sulfonyl 1,2,3-Triazoles
306 Citations2009Stepan Chuprakov, Sen Wai Kwok +3 more
Chemical CommunicationsOrganocatalytic reactions in water
292 Citations2009Monika Raj, Vinod K. Singh
This feature article has described reactions promoted by organocatalysts in a large excess of water, without any organic solvent or excess of any reactant.
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
Chemical CommunicationsRecent efforts directed to the development of more sustainable asymmetric organocatalysis
251 Citations2012José G. Hernández, Eusebio Juaristi
This feature article reviews some of the remarkable advancements that have made it possible to develop even more sustainable asymmetric organocatalyzed methodologies.
Chemical ReviewsNatural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids
251 Citations2007Farina Brackmann, Armin de Meijere
Catalysis Science & TechnologyAsymmetric organocatalytic reactions by bifunctional amine-thioureas
228 Citations2011Woon‐Yew Siau, Jian Wang
Chemistry - A European JournalCatalytic Asymmetric Carbon–Carbon Bond-Forming Reactions in Aqueous Media
225 Citations2002Kei Manabe, Shu̅ Kobayashi
Journal of the American Chemical SocietyA General and Efficient Cobalt(II)-Based Catalytic System for Highly Stereoselective Cyclopropanation of Alkenes with α-Cyanodiazoacetates
209 Citations2010Shifa Zhu, Xue Xu +2 more
The Co(II)-based catalytic system can be operated in a one-time protocol under mild conditions, affording the desired cyclopropane products in high yields with both high diastereo- and enantioselectivity.
Angewandte Chemie International EditionEnantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts
202 Citations2006Carin C. C. Johansson, Nadine Bremeyer +4 more
Organic & Biomolecular ChemistryIn water, on water, and by water: mimicking nature's aldolases with organocatalysis and water
198 Citations2010Nobuyuki Mase, Carlos F. Barbas
This work reviews recent developments and applications of aldolase-type organocatalytic direct transformations in aqueous media without addition of organic solvent.
Journal of the American Chemical SocietyHighly Asymmetric Intramolecular Cyclopropanation of Acceptor-Substituted Diazoacetates by Co(II)-Based Metalloradical Catalysis: Iterative Approach for Development of New-Generation Catalysts
198 Citations2011Xue Xu, Hongjian Lu +5 more
The [Co(P2)]-based intramolecular metalloradical cyclopropanation provides convenient access to densely functionalized 3-oxabicyclo[3.1.0]hexan-2-one derivatives bearing three contiguous quaternary and tertiary chiral centers with high enantiomeric purity.
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 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.
Journal of the American Chemical SocietyAsymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor Diazo Compounds: <i>p</i>-Methoxyphenyl Ketone as a General Stereoselectivity Controlling Group
172 Citations2011Vincent N. G. Lindsay, Cyril Nicolas +1 more
Different diacceptor diazo compounds bearing an α-PMP-ketone group were found to be effective carbene precursors for the highly stereoselective Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of alkenes (EWG = NO, CN, CO(2)Me).
Chemistry - A European JournalOne‐Pot Organocatalytic Domino Michael/α‐Alkylation Reactions: Direct Catalytic Enantioselective Cyclopropanation and Cyclopentanation Reactions
156 Citations2008Ismail Ibrahem, Gui‐Ling Zhao +5 more
One-pot combinations of amine and heterocyclic carbene catalysis (AHCC) enabled the highly enantioselective synthesis of beta-malonate esters from the reaction between bromomalonates and enals.
Chemistry - A European JournalOrganocatalytic Michael–Alkylation Cascade: The Enantioselective Nitrocyclopropanation of Oxindoles
153 Citations2011Fabio Pesciaioli, Paolo Righi +3 more
Chemistry - A European JournalDiastereodivergent Synthesis of 3‐Spirocyclopropyl‐2‐oxindoles through Direct Enantioselective Cyclopropanation of Oxindoles
138 Citations2012Xiaowei Dou, Yixin Lü
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.
Journal of the American Chemical SocietyOxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers
116 Citations2011Lizhu Gao, Geum‐Sook Hwang +1 more
A catalytic synthetic route to highly functionalized chiralcyclopropane derivatives was developed by Michael-initiated cyclopropanation of α-substituted acroleins with aryl- and alkyl diazoacetates with high to excellent diastereoselectivity.
The Journal of Organic ChemistryNucleophilic Addition of Phenol Derivatives to Methyl 1-Nitrocyclopropanecarboxylates
114 Citations2008Olga Lifchits, Dino Alberico +2 more
The methodology was applied in an enantioselective synthesis of the norepinephrine reuptake inhibitor atomoxetine (Strattera) and affords the products in good yields and with complete preservation of the enantiomeric excess at C-4.
The Journal of Organic ChemistryAn Expedient and Practical Method for the Synthesis of a Diverse Series of Cyclopropane α-Amino Acids and Amines
113 Citations2004Ryan P. Wurz, André B. Charette
A "one-pot" procedure involving sequential cyclopropanation and reduction is described, and the method can also be applied to the preparation of arylcyclopropyl amines.
Journal of the American Chemical SocietyOn the Mechanism of Ylide-Mediated Cyclopropanations: Evidence for a Proton-Transfer Step and Its Effect on Stereoselectivity
111 Citations2010S. Riches, Chandreyee Saha +4 more
By applying this model to S-, N-, and P-ylides the authors have been able to rationalize the outcome of different ylide reactions bearing a variety of substituents in terms of chemo- and enantioselectivity.
Angewandte Chemie International EditionConstruction of Asymmetric Quaternary Carbon Centers with High Enantioselectivity
110 Citations2011Masaki Shimizu
Organic LettersCatalytic Asymmetric Domino Michael Addition−Alkylation Reaction: Enantioselective Synthesis of Dihydrofurans
107 Citations2010Magnus Rueping, Alejandro Parra +3 more
A catalytic enantioselective synthesis of dihydrofurans has been developed providing mild and efficient access to diverse polysubstituted diHydrofuran in good yields and enantiOSElectivities.
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.
Chemical CommunicationsEnantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis
104 Citations2012Anup Biswas, Suman De Sarkar +2 more
Chemical CommunicationsAsymmetric oxidative Lewis base catalysis—unifying iminium and enamine organocatalysis with oxidations
101 Citations2012Magnus Rueping, Henrik Sundén +2 more
The one pot domino oxidation-iminium activation represents a convenient strategy for the enantioselective addition of malonates to allylic alcohols and the asymmetric formation of formyl cyclopropanes.
Chemical CommunicationsPhase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles
97 Citations2012Claudia Del Fiandra, Linda Piras +4 more
Heavily substituted cyclopropane esters were prepared in high yields, complete diastereoselection and high enantioselectivity, and allowed multi-gram preparation of desired products.
Organic LettersHighly Enantioselective Synthesis of Nitrocyclopropanes via Organocatalytic Conjugate Addition of Bromomalonate to α,β-Unsaturated Nitroalkenes
93 Citations2009Yi‐ning Xuan, Shao‐Zhen Nie +3 more
Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation.
Chemistry - A European JournalEnantioselective Synthesis of Functionalized Nitrocyclopropanes by Organocatalytic Conjugate Addition of Bromonitroalkanes to α,β‐Unsaturated Enones
91 Citations2008Jian Lv, Jiaming Zhang +2 more
A general enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of a variety of bromonitroalkanes to alpha,beta-unsaturated enone systems is presented.
Organic LettersBoronate Urea Activation of Nitrocyclopropane Carboxylates
82 Citations2011Sonia S. So, Tyler J. Auvil +2 more
A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks in good yields.
The Journal of Organic ChemistryAsymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by <i>C</i><sub>2</sub>-Symmetric Ureas
80 Citations2010Ying Cheng, Jing An +5 more
The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst.
Journal of the American Chemical Society<i>In Situ</i> Generation of Zinc Carbenoids from Diazo Compounds and Zinc Salts: Asymmetric Synthesis of 1,2,3-Substituted Cyclopropanes
78 Citations2009Sébastien R. Goudreau, André B. Charette
Chemistry - A European JournalOrganocatalyzed Cyclopropanation of α‐Substituted α,β‐Unsaturated Aldehydes: Enantioselective Synthesis of Cyclopropanes Bearing a Chiral Quaternary Center
77 Citations2010Vincent Terrasson, Arie van der Lee +2 more
An enantioselective cyclopropanation of alpha-substituted alpha,beta-unsaturated aldehydes with bromomalonate with optically activecyclopropane derivatives is successfully developed through a domino Michael/alpha-alkylation strategy.
Journal of the American Chemical SocietyEnantioselective Synthesis of 1,2,3-Trisubstituted Cyclopropanes Using <i>gem</i>-Dizinc Reagents
71 Citations2009Lucie E. Zimmer, André B. Charette
The first asymmetric cyclopropanation of allylic alcohols using gem-dizinc carbenoids, which allows the synthesis of 1,2,3-substitutedcyclopropane derivatives in high yields and excellent enantio- and diastereoselectivities, is reported.
Chemistry - A European JournalChiral Bis(oxazolinyl)phenyl Ru<sup>II</sup> Catalysts for Highly Enantioselective Cyclopropanation
66 Citations2010Jun‐ichi Ito, Satoshi Ujiie +1 more
European Journal of Organic ChemistrySynthesis of Activated Cyclopropanes by an MIRC Strategy: An Enantioselective Organocatalytic Approach to Spirocyclopropanes
63 Citations2011Alessio Russo, Sara Meninno +2 more
Angewandte Chemie International EditionEfficient Construction of α‐Spirocyclopropyl Lactones: Iridium–Salen‐Catalyzed Asymmetric Cyclopropanation
62 Citations2009Masami Ichinose, Hidehiro Suematsu +1 more
Three- and seven- Membered rings were constructed by the title reaction of terminal olefins with vinyldiazolactone as a carbene source, and the seven-membered rings upon subsequent hydrolysis and Cope rearrangement when 1,3-dienes were used.
The Journal of Organic ChemistryHighly Selective Ylide-Initiated Michael Addition/Cyclization Reaction for Synthesis of Cyclohexadiene Epoxide and Vinylcyclopropane Derivatives
61 Citations2010Ben‐Hu Zhu, Rui Zhou +5 more
On the basis of the reactions of camphor-derived sulfur ylide with alpha,beta-unsaturated ketone, highly efficient and selective synthesis of optically active cyclohexadiene epoxides and vinylcyclopropanes with excellent diastereoselectivity, moderate to high enantioselectivities, and yields has been achieved.
Organic & Biomolecular ChemistryAsymmetric epoxidation of 2-arylidene-1,3-diketones: facile access to synthetically useful epoxides
53 Citations2010Alessio Russo, Alessandra Lattanzi
The first enantioselective epoxidation reaction of acyclic and cyclic 2-arylidene-1,3-diketones is reported, which results in densely functionalised epoxide derivatives.
Chemistry - A European JournalFinal Elucidation of the Absolute Configuration of the Signal Metabolite Hormaomycin
47 Citations2004Boris D. Zlatopolskiy, Karin V. Loscha +5 more
The complete absolute configuration of hormaomycin 1 a has been established by HPLC and HPLC/MS experiments with appropriately derivatized 4-propylprolines, (2S,4S)-6 and (2R,4R)-6, as well as 4-(Z)-propenylpro lines, cis-5 and trans-5.
TetrahedronA new type of organocatalyst for highly stereoselective Michael addition of ketones to nitroolefins on water
45 Citations2009Siang-en Syu, Tzu-Ting Kao +1 more
The Journal of Organic ChemistrySynthesis of 3-(trans-2'-Nitrocyclopropyl)alanine, a Constituent of the Natural Peptide-Lactone Hormaomycin
42 Citations1995Juergen Zindel, Armin de Meijere
TetrahedronCatalytic asymmetric synthesis of nitrocyclopropane carboxylates
38 Citations2011Benoît Moreau, Dino Alberico +2 more
Organic LettersModular, Parallel Synthesis of an Illudinoid Combinatorial Library
37 Citations2003Michael C. Pirrung, Hao Liu
A library of 49 illudinoids was prepared via a three-step synthesis using a parallel synthesizer and solid-phase extractive purification, which revealed library members that inhibit nonsmall cell lung cancer.
Tetrahedron LettersRing opening of 1,1-dinitrocyclopropane by addition of C, N, O and S nucleophiles
35 Citations2005Екатерина М. Будынина, Оlga А. Ivanova +3 more
Chemical CommunicationsEnantioselective synthesis of substituted pyrans via amine-catalyzed Michael addition and subsequent enolization/cyclisation
31 Citations2012Utpal Das, Chan-Hui Huang +1 more
An organocatalytic construction of optically enriched substituted pyran derivatives via amine-catalyzed Michael addition and subsequent enolization/cyclisation has been described starting from electronically poor alkenes.
Russian Chemical ReviewsNitrocyclopropanes: synthesis and properties
30 Citations2009Elena B. Averina, N. V. Yashin +2 more
Tetrahedron LettersSynthesis and reactions of hydroxyspiro[5.2]cyclooctenones based on the cyclization of the dianions of acetone and diethyl 2-oxopropylphosphonate with 1,1-diacylcyclopropanes
11 Citations2008Nasır Rasool, Muhammad A. Rashid +3 more
TetrahedronSynthesis and reactions of functionalized spirocyclopropanes by cyclization of dilithiated β-ketosulfones, α-cyanoacetone and diethyl 2-oxopropylphosphonate with 1,1-diacetylcyclopropane
9 Citations2008Nasır Rasool, Muhammad A. Rashid +3 more
