Journal
TETRAHEDRON
Volume 89, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132089
Keywords
Michael addition; alpha,beta-unsaturated carboxylic acid; Asymmetric catalyst; Thiourea; Arylboronic acid
Categories
Funding
- KAKENHI [16H06384]
- Japan Society for the Promotion of Science [23105007]
- Ministry of Education, Culture, Sports, Science and Technology of Japan
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This review summarizes the first catalytic asymmetric Michael addition of heteroatomic nucleophiles to alpha,beta-unsaturated carboxylic acids. Hybrid catalysts are designed to activate the unsaturated carboxylic acids, leading to synthetic applications to biologically active compounds. The mechanistic consideration of multicomponent borate complexes is also discussed in this work.
The first catalytic asymmetric Michael addition of heteroatomic nucleophiles to alpha,beta-unsaturated carboxylic acids is summarized. Direct Michael addition is one of the most straightforward and atom-economical methods for constructing pharmaceutically beneficial building blocks and intermediates, although unsaturated carboxylic acids are known to be inactive Michael acceptors. We designed hybrid catalysts comprising arylboronic acid, thiourea, and tertiary amine to activate the unsaturated carboxylic acids. This review describes the aza- and thia-Michael additions using chiral multifunctional hybrid catalysts, their synthetic applications to biologically active compounds, and the mechanistic consideration of multicomponent borate complexes. (C) 2021 Elsevier Ltd. All rights reserved.
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