Huang Group
School of Chemical Biology & Biotechnology

Jiean Chen and Sixuan Meng’s work has been published in Chem. Sci.!


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

Jiean Chen, Sixuan Meng, Leming Wang, Hongmei Tang and Yong Huang*, Chem. Sci. 2015, 6, 4184.

We report thefirst asymmetric sulfa-Michael addition (SMA) reactions using a chiralN-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.