2015
DOI: 10.1039/c5sc00878f
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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.

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Cited by 115 publications
(44 citation statements)
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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 [27], versatile organocatalysts [810], and starting materials for heterocycle syntheses [1113]. 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 [1920], and catalysis [2122], to biological activities of NHC complexes [2324].…”
Section: Introductionmentioning
confidence: 99%
“…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 [27], versatile organocatalysts [810], and starting materials for heterocycle syntheses [1113]. 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 [1920], and catalysis [2122], to biological activities of NHC complexes [2324].…”
Section: Introductionmentioning
confidence: 99%
“…[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%
“…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%