Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst

Chen, Jiean; Meng, Sixuan; Wang, Leming; Tang, Hongmei; Huang, Yong

doi:10.1039/c5sc00878f

Cited by 112 publications

(44 citation statements)

References 103 publications

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“…Since the first isolation of a stable N-heterocyclic carbene (NHC) [1] in 1991 this compound class has provided numerous highly efficient ligands of NHC-metal catalysts for cross-coupling reactions [2–7], versatile organocatalysts [8–10], and starting materials for heterocycle syntheses [11–13]. Consequently books [14–16] and reviews cover the range from NHC structures in the light of their early history [17], syntheses [6,18], coordination chemistry [19–20], and catalysis [21–22], to biological activities of NHC complexes [23–24].…”

Section: Introductionmentioning

confidence: 99%

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

Liu

Namyslo

Nieger

et al. 2016

Beilstein J. Org. Chem.

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The mesomeric betaine imidazolium-1-ylphenolate forms a borane adduct with tris(pentafluorophenyl)borane by coordination with the phenolate oxygen, whereas its NHC tautomer 1-(2-phenol)imidazol-2-ylidene reacts with (triphenylphosphine)gold(I) chloride to give the cationic NHC complex [Au(NHC)2][Cl] by coordination with the carbene carbon atom. The anionic N-heterocyclic carbene 1-(2-phenolate)imidazol-2-ylidene gives the complexes [K][Au(NHC−)2], [Rh(NHC−)3] and [Ni(NHC−)2], respectively. Results of four single crystal analyses are presented.

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Section: Introductionmentioning

confidence: 99%

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

Liu

Namyslo

Nieger

et al. 2016

Beilstein J. Org. Chem.

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“…[57] As shown in the Scheme, HFIP enabled the thia-Michael addition by engaging in a dual interaction with both chalcones 109 and aminothiophenol 110. Furthermore, as previously reported, [58] HFIP might serve as a proton shuttle to achieve the proton shift from the thiol to the first anionic Michael adduct 112. Finally, the following intramolecular nucleophilic attack of the amino group to the carbonyl gave rise to the 2,3-dihydro-1,5benzothiazepines.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 53%

Fluorinated Alcohols: Magic Reaction Medium and Promoters for Organic Synthesis

Xiao

2019

The Chemical Record

110

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Fluorinated alcohols have been widely used in the synthetic organic chemistry over the past decades. The unique properties such as the strong hydrogen‐bonding donor ability and low nucleophilicity allow them to promote organic reactions in the absence of any catalyst. These approaches have distinct advantages in terms of operational simplicity, practicability and environmental friendliness. Reactions promoted by fluorinated alcohols, including nucleophilic substitution reactions, annulation reactions, electrophilic reactions, dearomatization reactions, functionalization of multiple bond, epoxidation reactions and miscellaneous reactions have been summarized in this account.

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“…One year later, the same group reported an enantioselective sulfa‐Michael addition reaction of mercaptans with electron‐deficient alkenes by using chiral NHC 8 as a Brønsted basic catalyst (Scheme ) . This method was used to effectively construct quaternary chiral centers that contained CF 3 and S functionalities with excellent enantioselectivities.…”

Section: Brønsted Base Catalystsmentioning

confidence: 99%

Enantioselective Reactions Catalyzed by N‐Heterocyclic Carbenes

et al. 2017

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Enantioselective organocatalysis by using N-heterocyclic carbenes (NHCs) has emerged as ap owerful strategy for the construction of complex chiral molecules. Recently, remarkablea dvances have been made in enantioselective NHC-catalyzed reactions that involved iversea ctivation intermediates, such as Breslow intermediates, homoenolate intermediates, a,b-unsaturated acylazoliums, azolium enolates, and azolium dienolates, which are generated by the nucleophilic addition of NHCs to aldehydes. Furthermore, NHC-catalyzed reactions that proceed through non-covalent bonding interactions have also been developed.

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Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst

Abstract: Enantioselective asymmetric sulfa-Michael addition (SMA) reactions using a chiral N-heterocyclic carbene as a non-covalent organocatalyst.

Cited by 112 publications

References 103 publications

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

Fluorinated Alcohols: Magic Reaction Medium and Promoters for Organic Synthesis

Enantioselective Reactions Catalyzed by N‐Heterocyclic Carbenes

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