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Updated: Feb 17, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent
Jiean Chen1, Sixuan Meng1, Leming Wang1
1Key Laboratory of Chemical Genomics , School of Chemical Biology and Biotechnology , Peking University , Shenzhen Graduate School , Shenzhen , 518055 , China .
Abstract:
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 CF3 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.
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