N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones
Chemical SciencePublished 1 January 2011Open access
Roxanne L. Atienza, Howard S. Roth, Karl A. Scheidt
Citations90
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
Preliminary mechanistic studies support a new conjugate addition/Umpolung process involving the ejection and subsequent unusual re-addition of a sulfinate ion.
Abstract
N-heterocyclic carbenes catalyze the rearrangement of 1,1-bis(arylsulfonyl)ethylene to the corresponding trans-1,2-bis(phenylsulfonyl) under mild conditions. Tandem rearrangement/cycloadditions have been developed to capitalize on this new process and generate highly substituted isoxazolines and additional heterocyclic compounds. Preliminary mechanistic studies support a new conjugate addition/Umpolung process involving the ejection and subsequent unusual re-addition of a sulfinate ion.
Keywords
Chemistry
Chemical ReviewsOrganocatalysis by N-Heterocyclic Carbenes
3,014 Citations2007Dieter Enders, Oliver Niemeier +1 more
The inversion of the classical reactivity (Umpolung) opens up new synthetic pathways in biochemical processes as nucleophilic acylations and in nature, the coenzyme thiamine (vitamin B1), a natural thiazolium salt, utilizes a catalytic variant of this concept in biochemical process as nucleophile acylation.
Angewandte Chemie International Edition in English1,3‐Dipolar Cycloadditions. Past and Future
2,840 Citations1963Rolf Huisgen
Angewandte Chemie International EditionIn the Golden Age of Organocatalysis
2,574 Citations2004Peter I. Dalko, Lionel Moisan
The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
Chemical ReviewsSmall-Molecule H-Bond Donors in Asymmetric Catalysis
2,574 Citations2007Abigail G. Doyle, Eric N. Jacobsen
NatureThe advent and development of organocatalysis
2,351 Citations2008David W. C. MacMillan
My opinion on why the field of organocatalysis has blossomed so dramatically over the past decade is presented.
Journal of the American Chemical SocietyOn the Mechanism of Thiamine Action. IV.<sup>1</sup> Evidence from Studies on Model Systems
1,662 Citations1958Ronald Breslow
Chemical Society ReviewsOrganocatalysis—after the gold rush
1,272 Citations2009Søren Bertelsen, Karl Anker Jørgensen
This tutorial review will firstly sketch the basic developments in organocatalysis, focussing especially on the use of secondary amines as catalysts for the functionalization of aldehydes and alpha,beta-unsaturated aldeHydes, with emphasis on the mechanisms of the transformations and outline recent trends within central areas of this research topic.
Angewandte Chemie International EditionLewis Base Catalysis in Organic Synthesis
1,239 Citations2008Scott E. Denmark, Gregory L. Beutner
It has become increasingly apparent that the behavior of Lewis bases as agents for promoting chemical reactions is not merely as an electronic complement of the cognate Lewis acids: in fact Lewis bases are capable of enhancing both the electrophilic and nucleophilic character of molecules to which they are bound.
Accounts of Chemical ResearchNucleophilic Carbenes in Asymmetric Organocatalysis
1,040 Citations2004Dieter Enders, Tim Balensiefer
After a long and difficult search, stable carbenes are finally isolated, characterized, and in the chemist's hands, and the experiments of decades have finally resulted in successful enantioselective benzoin condensations and enantiOSElective intramolecular Stetter reactions.
Chemical CommunicationsThe ying and yang of asymmetric aminocatalysis
816 Citations2006Benjamin List
An overview of asymmetric catalysis of carbonyl transformations via iminium ion and enamine intermediates using chiral amines as organocatalysts has been given and their recent merger in tandem sequences is discussed.
Angewandte Chemie International EditionOrganocatalyzed Conjugate Umpolung of α,β‐Unsaturated Aldehydes for the Synthesis of γ‐Butyrolactones
722 Citations2004Christian Burstein, Frank Glorius
Journal of the American Chemical Society<i>N</i>-Heterocyclic Carbene-Catalyzed Generation of Homoenolates: γ-Butyrolactones by Direct Annulations of Enals and Aldehydes
701 Citations2004Stephanie S. Sohn, E.L. Rosen +1 more
This process demonstrates an unprecedented reaction mode for the generation of nucleophilic carbanions with a multifunctional organocatalyst under exceptionally mild and convenient reaction conditions.
Chemical Society ReviewsRecent advances in carbon–carbon bond-forming reactions involving homoenolates generated by NHC catalysis
642 Citations2008Vijay Nair, Sreekumar Vellalath +1 more
The versatility of NHC-bound homoenolate is illustrated by its annulation with various carbonyl compounds leading to gamma-butyrolactones, spiro-gamma- butyrolactsones, and delta-lactones.
Journal of the American Chemical SocietyA Highly Enantioselective Catalytic Intramolecular Stetter Reaction
498 Citations2002Mark S. Kerr, Javier Read de Alaniz +1 more
A family of chiral triazolium salts has been developed for inducing the asymmetric intramolecular Stetter reaction, with optimal results, with the product keto esters formed in 82-97% ee and very good chemical yield.
Journal of the American Chemical SocietyNHC Catalyzed Oxidations of Aldehydes to Esters: Chemoselective Acylation of Alcohols in Presence of Amines
493 Citations2010Suman De Sarkar, Stefan Grimme +1 more
Topics in current chemistryChiral Brønsted Acids for Asymmetric Organocatalysis
472 Citations2009Daniela Kampen, Corinna M. Reisinger +1 more
Angewandte Chemie International EditionAn Efficient Nucleophilic Carbene Catalyst for the Asymmetric Benzoin Condensation
452 Citations2002Dieter Enders, Ulrike Kallfass
Nature ChemistryCooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams
387 Citations2010Dustin E. A. Raup, Benoit Cardinal‐David +2 more
A cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones, generating highly substituted γ-lactams in moderate to good yields and with high levels of diastereo- and enantioselectivity.
Topics in current chemistryChiral Brønsted Acids for Asymmetric Organocatalysis
370 Citations2009Daniela Kampen, Corinna M. Reisinger +1 more
This work has shown that certain carbonyl compounds can be activated through these stronger Brønsted acid catalysts and, in dealing with sensitive substrate classes, chiral dicarboxylic acids proved of particular value.
Journal of the American Chemical Society<i>N</i>-Heterocyclic Carbene-Catalyzed Reaction of Chalcones and Enals via Homoenolate: an Efficient Synthesis of 1,3,4-Trisubstituted Cyclopentenes
345 Citations2006Vijay Nair, Sreekumar Vellalath +2 more
Nucleophilic heterocyclic carbene-catalyzed cyclopentannulation of enals and chalcones via homoenolate has been observed for the first time and leads to a very efficient synthesis of 3,4-trans-disubstituted-1-arylcyclopentenes instead of the expected cyclopENTanones.
Organic LettersConversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes
344 Citations2005Audrey Chan, Karl A. Scheidt
N-Heterocyclic carbenes derived from benzimidazolium salts are effective catalysts for generating homoenolate species from alpha,beta-unsaturated aldehydes and a kinetic resolution of secondary alcohols can be achieved using chiral imidazoylidene catalysts.
Journal of the American Chemical SocietyCooperative <i>N</i>-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates
322 Citations2010Benoit Cardinal‐David, Dustin E. A. Raup +1 more
A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivities and enantioselectivity.
Journal of the American Chemical SocietyHighly Stereoselective Formal [3 + 3] Cycloaddition of Enals and Azomethine Imines Catalyzed by <i>N</i>-Heterocyclic Carbenes
320 Citations2007Audrey Chan, Karl A. Scheidt
This formal [3 + 3] cycloaddition between α,β-unsaturated aldehydes and azomethine imines catalyzed by NHC has been developed to give substituted pyridazinones in good to excellent yields with high diastereoselectivity (>20:1).
Angewandte Chemie International Edition in EnglishCycloadditions — Definition, Classification, and Characterization
315 Citations1968R. Huisgen
Journal of the American Chemical SocietyCatalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of β-Hydroxyesters from Epoxyaldehydes
313 Citations2004Kenneth Yu‐Kin Chow, Jeffrey W. Bode
This chemistry unveils a mechanistically viable solution to the catalytic, waste-free synthesis of esters, and provides a new method for the synthesis of anti-aldol adducts.
Helvetica Chimica ActaThe First Asymmetric Intramolecular <i>Stetter</i> Reaction. Preliminary Communication
297 Citations1996Dieter Enders, Klaus Breuer +2 more
ChemInformN‐Heterocyclic Carbene‐Catalyzed Reaction of Chalcones and Enals via Homoenolate: An Efficient Synthesis of 1,3,4‐Trisubstituted Cyclopentenes.
287 Citations2006Vijay Nair, Sreekumar Vellalath +2 more
Organic LettersTandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes
286 Citations2006Brooks E. Maki, Audrey Chan +2 more
N-heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields in good yields.
PubMedDiscovering New Reactions with N-Heterocyclic Carbene Catalysis.
283 Citations2009Eric M. Phillips, Audrey Chan +1 more
The successful isolation of carbenes with less bulky substituents demonstrates that electronic factors may have greater impact on the stability of the carbene than steric ones.
Journal of the American Chemical SocietyEnantioselective Protonation of Catalytically Generated Chiral Enolates as an Approach to the Synthesis of α-Chloroesters
271 Citations2005Nathan T. Reynolds, Tomislav Rovis
Treatment of alpha,alpha-dichloroaldehydes with various phenols in the presence of chiral triazolium salt catalysts and excess base results in the synthesis of alpha-chloro aryl esters in good yield and enantioselectivity.
Angewandte Chemie International EditionAsymmetric Organocatalysis with Sulfones
269 Citations2010Martin Nielsen, Christian Jacobsen +3 more
Sulfones have become especially important substrates in the field of organocatalysis because of the many transformation possibilities and their ability to generate both nucleophilic and electrophilic reaction partners.
Journal of the American Chemical SocietyUmpolung of Michael Acceptors Catalyzed by <i>N</i>-Heterocyclic Carbenes
269 Citations2006Christian A. Fischer, Sean W. Smith +2 more
N-Heterocyclic carbenes can catalyze beta-alkylations of a range of alpha,beta-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes through an unanticipated addition-tautomerization sequence.
Organic Letters<i>N</i>-Heterocyclic Carbene-Catalyzed Oxidation of Unactivated Aldehydes to Esters
230 Citations2008Brooks E. Maki, Karl A. Scheidt
N-Heterocyclic carbenes catalyze the oxidation of unactivated aldehydes to esters with manganese(IV) oxide in excellent yield and successfully oxidize potentially epimerizable aldeHydes and alcohols while preserving stereochemical integrity.
Helvetica Chimica ActaA Novel Asymmetric Benzoin Reaction Catalyzed by a Chiral Triazolium Salt. Preliminary communication
216 Citations1996Dieter Enders, Klaus Breuer +1 more
Angewandte Chemie International EditionA Highly Enantioselective Intramolecular Michael Reaction Catalyzed by N‐Heterocyclic Carbenes
211 Citations2007Eric M. Phillips, Manabu Wadamoto +2 more
N-heterocyclic carbenes (NHCs) are highly selective catalysts for the intramolecular Michael reaction of substrates 1 to afford dicarbonyl compounds 2 after the addition of an exogenous nucleophile.
Journal of the American Chemical SocietyCatalytic Intramolecular Crossed Aldehyde−Ketone Benzoin Reactions: A Novel Synthesis of Functionalized Preanthraquinones
187 Citations2003Yoshifumi Hachisu, Jeffrey W. Bode +1 more
The first crossed aldehyde-ketone benzoin reaction in excellent yield under mild reaction conditions offers a convenient approach to sophisticated molecular architectures useful for the stereocontrolled construction of polycyclic compounds as well as the fully regiocontrolling synthesis of anthra- and naphthoquinones.
Chemical ReviewsMultiply convergent syntheses via conjugate-addition reactions to cycloalkenyl sulfones
183 Citations1986P. L. Fuchs, T. F. BRAISH
Organic LettersFirst Organocatalyzed Asymmetric Michael Addition of Aldehydes to Vinyl Sulfones
181 Citations2005Sarah Mossé, Alexandre Alexakis
The determination of absolute configuration allowed us to postulate a Si,Si transition state model, as shown previously for nitroolefins, and 1,4-Adducts are obtained in good yields and enantioselectivities.
Journal of the American Chemical SocietyHighly Diastereo- and Enantioselective Additions of Homoenolates to Nitrones Catalyzed by <i>N</i>-Heterocyclic Carbenes
175 Citations2008Eric M. Phillips, Troy E. Reynolds +1 more
The diastereo- and enantioselective addition of N-heterocyclic carbene-generated homoenolates to nitrones is reported and unusual morpholinone heterocycles are generated which are converted into γ-hydroxy amino esters by addition of methanol to the reaction.
Journal of the American Chemical SocietyDirect Amination of Homoenolates Catalyzed by <i>N</i>-Heterocyclic Carbenes
170 Citations2008Audrey Chan, Karl A. Scheidt
This formal [3+2] cycloaddition between alpha,beta-unsaturated aldehydes and acylaryldiazenes, catalyzed by an N-heterocyclic carbene, produces substituted pyrazolidinones in good yields.
Journal of the American Chemical SocietyHydroacylation of Activated Ketones Catalyzed by <i>N</i>-Heterocyclic Carbenes
157 Citations2006Audrey Chan, Karl A. Scheidt
Preliminary mechanistic evidence indicates that the reduction and acylation steps are sequential operations and the intramolecular variant of this organocatalytic reaction affords benzofuranones in good yield.
Organic Letters3,3‘-Bimorpholine Derivatives as a New Class of Organocatalysts for Asymmetric Michael Addition
139 Citations2006Sarah Mossé, Marju Laars +3 more
New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone, with good to high levels of diastereo- and enantioselectivity.
The Journal of Organic ChemistryN-Heterocyclic Carbene Catalyzed Aza-Morita−Baylis−Hillman Reaction of Cyclic Enones with <i>N</i>-Tosylarylimines
131 Citations2007Lin He, Tengyue Jian +1 more
Crossover experiments show NHC can add to N-tosylarylimines in a reversible manner, which allows the addition of NHC to cyclic enones and thus catalyzes the aza-Mortia-Baylis-Hillman reaction.
Helvetica Chimica ActaStereoselektivität und Reaktivität bei der 1,3‐dipolaren Cycloaddition chiraler <i>N</i>‐(Alkoxyalkyl)nitrone
131 Citations1977Andrea Vasella
TetrahedronN-Heterocyclic carbene-catalyzed oxidations
130 Citations2008Brooks E. Maki, Audrey Chan +2 more
N-Heterocyclic carbenes catalyze the oxidation of allylic and benzylic alcohols as well as saturated aldehydes to esters with manganese(IV) oxide in excellent yields, resulting in a variety of esters that can be synthesized, including protected carboxylates.
Organic LettersEnantioselective Conjugate Addition of Nitroalkanes to Vinyl Sulfone: An Organocatalytic Access to Chiral Amines
130 Citations2009Qiang Zhu, Yixin Lü
The described method, in combination with ready desulfonation, represents a novel approach to access alpha-alkylated chiral amines.
Angewandte Chemie International EditionAccess to High Levels of Molecular Complexity by One‐Pot Iridium/Enamine Asymmetric Catalysis
124 Citations2011Adrien Quintard, Alexandre Alexakis +1 more
A catalytic sequence that exploits the compatibility of (chiral) cationic iridium catalysts for the isomerization of primary allylic alcohols to aldehydes with organocatalysts showed useful generality with respect to both the nucleophile and the electrophile.
Angewandte ChemieRadical‐Mediated Alkenylation, Alkynylation, Methanimination, and Cyanation of <i>B</i>‐Alkylcatecholboranes
117 Citations2006Arnaud‐Pierre Schaffner, Vincent Darmency +1 more
Journal of the American Chemical Society<i>N</i>-Heterocyclic Carbene-Catalyzed Enantioselective Mannich Reactions with α-Aryloxyacetaldehydes
114 Citations2009Yasufumi Kawanaka, Eric M. Phillips +1 more
N-Heterocyclic carbenes catalyze a new Mannich-type reaction to form beta-amino acid derivatives in high yield and enantioselectivity in a new carbene catalysis concept and the activated ester products formed in situ are manipulated to form a variety of useful compounds.
Chemical CommunicationsAsymmetric organocatalytic Michael addition of ketones to vinyl sulfone
113 Citations2008Qiang Zhu, Lili Cheng +1 more
Highly enantioselective organocatalytic Michael addition of ketones to vinyl sulfone catalyzed by a cinchona alkaloid-derived primary amine is reported for the first time.
Journal of the Chemical Society Perkin Transactions 11,3-Dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes
112 Citations2002Helen M. I. Osborn, Natasha Gemmell +1 more
Angewandte Chemie International EditionOne‐Pot Synthesis of α‐Amino Acids from Imines through CO<sub>2</sub> Incorporation: An Alternative Method for Strecker Synthesis
103 Citations2011Tsuyoshi Mita, Jianyang Chen +2 more
This work considered the use of a stannyl anion, which is known to react with imine 2 so that the resulting a-amino stannane 3 would act as a nucleophile towards CO2 after metal exchange with Sn.
The Journal of Organic ChemistryRadical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones
96 Citations2003Stefan Berlin, Cecilia Ericsson +1 more
Beta-hydroxyalkyl aryl chalcogenides obtained by regioselective ring-opening of epoxides with benzeneselenolate or -tellurolate were found to undergo efficient hetero-Michael addition when treated with ethyl propiolate.
Carbohydrate ResearchAcetonation of some pentoses with 2,2-dimethoxypropane-N,N-dimethylformamide-p-toluenesulfonic acid
92 Citations1976Makoto Kiso, Akira Hasegawa
Organic LettersOrganocatalytic Michael Addition of Aldehydes to Vinyl Sulfones: Enantioselective α-Alkylations of Aldehydes and Their Derivatives
89 Citations2008Qiang Zhu, Yixin Lü
The described enantioselective addition to vinyl sulfones, in combination with desulfonation, offers a unique, asymmetric entry to alpha-alkylated aldehydes and their derivatives.
The Journal of Organic ChemistryEnantioselective Synthesis of Aza-β-lactams via NHC-Catalyzed [2 + 2] Cycloaddition of Ketenes with Diazenedicarboxylates
88 Citations2009Xueliang Huang, Xiangyu Chen +1 more
N-Heterocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition of aryl(alkyl)ketenes and diazenedicarboxylates to give the corresponding aza-beta-lactams in good yields with up to 91% ee.
Journal of the American Chemical SocietySynthesis of the Fully Functionalized Bicyclic Core of Garsubellin A
87 Citations1999K. C. Nicolaou, Jeffrey A. Pfefferkorn +2 more
The Journal of Organic ChemistryAsymmetric total synthesis of (+)-negamycin and (-)-3-epinegamycin via enantioselective 1,3-dipolar cycloaddition
85 Citations1989K. KASAHARA, Hideo Iida +1 more
Organic LettersNHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins
85 Citations2008Eric M. Phillips, Manabu Wadamoto +3 more
N-heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4-dihydrocoumarins.
TetrahedronHydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems
84 Citations1993Deryk K. Thompson, Christine N. Hubert +1 more
An intermediate in one of the routes, ethyl 2,3, 6-trideoxy-3,6-imino-4,5:7,8-di- O -isopropylidene-D- glycero -L- altro -octonate, could be converted in two steps into a β-lactam.
Chemistry - A European JournalHighly Enantioselective Conjugate Additions of Aldehydes to Vinyl Sulfones
81 Citations2009Aitor Landa, M.A. Maestro +5 more
A diaryl prolinol silyl ether was found to catalyse efficiently and enantioselectively the conjugate addition of aldehydes to vinyl sulfones and the ample synthetic utility of the resulting adducts is illustrated.
Helvetica Chimica ActaSynthese und Umwandlungen von Isoxazolidin‐Nucleosiden
79 Citations1977Andrea Vasella
The Journal of Organic ChemistryAsymmetric induction in nitrone cycloadditions: a total synthesis of acivicin by double asymmetric induction
73 Citations1988Shadreck Mzengeza, Ralph A. Whitney
Angewandte Chemie International EditionA Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives
72 Citations2007Vijay Nair, Smitha C. Mathew +2 more
Two unexpected transformations: The reaction of the Huisgen zwitterion derived from triphenylphosphane and diisopropyl azodicarboxylate (DIAD) with chalcones affords functionalized pyrazolines and the reaction with dienones affordspyrazolopyridazines.
Angewandte Chemie International EditionOligopyrrole Synthesis by 1,3‐Dipolar Cycloaddition of Azomethine Ylides with Bissulfonyl Ethylenes
69 Citations2007Ana López‐Pérez, Rocío Robles‐Machín +2 more
Chemical and Pharmaceutical BulletinCatalytic Action of Azolium Salts. VIII. Oxidative Aroylation with Arenecarbaldehydes Catalyzed by 1,3-Dimethylbenzimidazolium Iodide.
69 Citations1997Akira Miyashita, Yumiko Suzuki +4 more
Journal of the American Chemical SocietyDesign of Structurally Rigid <i>trans</i>-Diamine-Based Tf-Amide Organocatalysts with a Dihydroanthracene Framework for Asymmetric Conjugate Additions of Heterosubstituted Aldehydes to Vinyl Sulfones
68 Citations2010Shin A. Moteki, Senmiao Xu +2 more
Journal of the Chemical Society Chemical CommunicationsElectron-transfer reductions by active aldehydes catalysed by thiazolium salt in the presence of triethylamine
66 Citations1980Hiroo Inoue, Kunihiko Higashiura
Organic LettersN-Heterocyclic Carbene-Catalyzed Silyl Enol Ether Formation
64 Citations2008Jinhua J. Song, Zhulin Tan +4 more
The Journal of Organic ChemistryHow important are secondary orbital interactions in favoring the endo mode in 1,3-dipolar cycloadditions of nitrones?
59 Citations1990Marina Burdisso, Remo Gandolfi +2 more
Tetrahedron LettersHighly selective cross-metathesis with phenyl vinyl sulphone using the ‘second generation’ Grubbs’ catalyst
58 Citations2001Karol Grela, Michał Bieniek
The Journal of Organic ChemistryHomochiral α-<scp>d</scp>- and β-<scp>d</scp>-Isoxazolidinylthymidines via 1,3-Dipolar Cycloaddition
56 Citations1999Ugo Chiacchio, Antonino Corsaro +6 more
Chemistry - A European JournalOrganocatalytic Addition on 1,2‐Bis(sulfone)vinylenes Leading to an Unprecedented Rearrangement
52 Citations2009Adrien Quintard, Alexandre Alexakis
An unprecedented rearrangement of 1,2-bis(sulfone)vinylenes used in aminocatalysis led to the formation of highly useful gem-disulfones, leading to highly versatile adducts using both ketones and aldehydes.
Organic LettersA New Class of Structurally Rigid Tricyclic Chiral Secondary Amine Organocatalyst: Highly Enantioselective Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones
52 Citations2011Jian Xiao, Yunpeng Lu +3 more
A new class of chiral secondary amine organocatalyst was rationally designed as an efficient catalyst to catalyze the elusive Michael addition of aldehydes to vinyl sulfones at room temperature without having to resort to high catalyst loading, anhydrous solvents, and low temperatures.
Topics in current chemistryCarbene Catalysts
51 Citations2009Jennifer L. Moore, Tomislav Rovis
A discussion of catalyst development and nucleophilic characteristics precedes a description of recent advancements and new reactions using N-heterocyclic carbenes in catalysis.
The Journal of Organic ChemistryStereoselective Synthesis of Cyclic Ethers Using Vinylogous Sulfonates as Radical Acceptors: Effect of <i>E</i>/<i>Z</i> Geometry and Temperature on Diastereoselectivity
46 Citations2000P. Andrew Evans, Thara Manangan
The level of stereocontrol in a 6-exo radical cyclization and may be attributed to the type of radical intermediate and the modest selectivity obtained may be a function of the acyl radical geometry (sp2) and high inversion barrier (29 kcal/mol).
Journal of the American Chemical SocietyPreparation and Some Subsequent Transformations of Tetraethynylmethane
43 Citations1994Ken S. Feldman, Carolyn K. Weinreb +2 more
Tetrahedron LettersA new synthesis of (2S)-4-oxopipecolic acid by thermal rearrangement of enantiopure spirocyclopropaneisoxazolidine
40 Citations1996Fabrizio Machetti, Franca M. Cordero +3 more
Journal of the American Chemical SocietyConsequences of fixing three parallel coplanar double bonds in close proximity with different geometries. Synthesis and spectral parameters of syn- and anti-sesquinorbornatriene
37 Citations1986Leo A. Paquette, H. KUENZER +5 more
Tetrahedron LettersVinylogous sulfonates as radical acceptors for the stereoselective synthesis of cyclic ethers
37 Citations1997P. Andrew Evans, Thara Manangan
European Journal of Organic ChemistryModified <i>B</i>‐Alkylcatecholboranes as Radical Precursors
36 Citations2010Monique Lüthy, Vincent Darmency +1 more
TetrahedronSteric effects vs secondary orbital interactions in nitrone cycloadditions
35 Citations1988Marina Burdisso, Anna Gamba +2 more
The Journal of Organic ChemistryAlkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans
34 Citations1991Albert Padwa, William H. Bullock +4 more
SynthesisPhenylsulfonylethylidene (PSE) Acetals: A Novel Protective Group in Carbohydrate Chemistry
34 Citations2001Florence Chéry, Patrick Rollin +2 more
The Journal of Organic Chemistry7-Oxabicyclo[2.2.1]hept-2-ene and related materials by reductive elimination
33 Citations1985Seid Mirsadeghi, Bruce Rickborn
SynthesisA Novel Route for the Synthesis of Unsaturated Oxo Sulfones and Bissulfones
33 Citations1999D. Bhaskar Reddy, N. Chandrasekhar Babu +2 more
Tetrahedron LettersCyclofunctionalisation of epoxyalcohol derivatives. 1. Delivery of functionalised carbon for stereospecific synthesis of dihydrofurans and dihydroxyacids
31 Citations1985Stuart W. McCombie, Bandarpalle B. Shankar +1 more
Tetrahedron LettersPhenylsulfonylethylidene (PSE) acetals as atypical carbohydrate-protective groups
26 Citations2000Florence Chéry, Patrick Rollin +2 more
Carbohydrate ResearchSynthesis of prumycin and related compounds
22 Citations1976Akira Hasegawa, Nobumitsu Aritake +1 more
Evidence in support of the structures assigned to the new derivatives of Prumycin is presented.
Organic LettersOxidative Addition of Pd(0) to Ar−SO<sub>2</sub>R Bonds: Heck-Type Reactions of Sulfones
22 Citations2006José Luis Garcı́a Ruano, José Alemán +1 more
1,2-Diphenylsulfonyl ethenes, alkynylphenyl sulfones, and other sulfones can transfer the aryl group to alkyl acrylates forming cinnamic esters, less prone to act as acceptors in the Heck-type reactions.
Angewandte ChemieA Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives
21 Citations2007Vijay Nair, Smitha C. Mathew +2 more
Justus Liebig s Annalen der ChemieKondensationen mit Methylendisulfonen
17 Citations1974Hermann Stetter, K. STEINBECK
Tetrahedron LettersDienophilic reactivity of Trans-1,2-bis(phenylsulphonyl)ethylene: A valid alternative to maleic anhydride
16 Citations1983Ottorino De Lucchi, Giorgio Modena
Tetrahedron LettersA novel effective electrophile: β-trifluoroacetylketene diphenyldithioacetal S , S -tetroxide
9 Citations2003Arkady L. Krasovsky, Sergej V. Druzhinin +2 more
The Journal of Organic ChemistryStereoselective Synthesis of Cyclic Ethers Using Vinylogous Sulfonates as Radical Acceptors: Effect of <i>E</i>/<i>Z</i> Geometry and Temperature on Diastereoselectivity.
8 Citations2000P. Andrew Evans, Thara Manangan
…