Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalystElectronic supplementary information (ESI) available. CCDC 1047559. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00878f

We report the first asymmetric sulfa-Michael addition (SMA) reactions using a chiral N -heterocyclic carbene (NHC) as a non-covalent organocatalyst. We demonstrate that a triazolium salt derived NHC functions as an excellent Brønsted base to promote enantioselective carbon-sulfur bond formation. The...

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Main Authors: Chen, Jiean, Meng, Sixuan, Wang, Leming, Tang, Hongmei, Huang, Yong
Format: Article
Language:English
Online Access:Get full text
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Summary:We report the first asymmetric sulfa-Michael addition (SMA) reactions using a chiral N -heterocyclic carbene (NHC) as a non-covalent organocatalyst. We demonstrate that a triazolium salt derived NHC functions as an excellent Brønsted base to promote enantioselective carbon-sulfur bond formation. The reaction is applicable to a wide range of thiols and electrophilic olefins. Notably, quaternary chiral centers bearing both an S atom and a CF 3 group were synthesized with excellent asymmetric control. Mechanistic studies suggest that the facial discrimination is likely to be guided by non-covalent interactions: hydrogen bonding and π-π stacking. Enantioselective asymmetric sulfa-Michael addition (SMA) reactions using a chiral N -heterocyclic carbene as a non-covalent organocatalyst.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc00878f