Journal
ACS CATALYSIS
Volume 11, Issue 10, Pages 6316-6324Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c01908
Keywords
organocatalysis; N-heterocyclic carbene; noncovalent catalysis; bifunctional catalysis; aza-Michael addition
Categories
Funding
- National Natural Science Foundation of China [21825101]
- Hong Kong RGC [16300320]
- Shenzhen Science and Technology Innovation Commission [SGDX2019081623241924]
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Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Chiral N-heterocyclic carbenes (NHCs) have been recently established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. The underlying HOMO-raising activation of nucleophiles takes advantage of the strong Bronsted basicity of NHCs. However, the scope of compatible electrophiles has been quite limited. In this article, we report a bifunctional NHC with an embedded hydrogen-bonding motif that shows remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction. The catalytic efficiency far exceeds that of the benchmark tertiary amine-thiourea scaffold.
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