Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 12, Pages 5627-5635Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12457
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Funding
- National Science Foundation [CHE-1806747, CHE-1856613, 1828064]
- NIGMS [R01 GM126283]
- XSEDE Science Gateways Program - National Science Foundation [ACI-1548562]
- University of Florida
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1828064] Funding Source: National Science Foundation
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beta-Amino esters are obtained with high levels of enantioselectivity via the conjugate addition of cyclic amines to unactivated alpha,beta-unsaturated esters. A related strategy enables the kinetic resolution of racemic cyclic 2-arylamines, using benzyl acrylate as the resolving agent. Reactions are facilitated by an unprecedented selenourea-thiourea organocatalyst. As elucidated by DFT calculations and C-13 kinetic isotope effect studies, the ratelimiting and enantiodetermining step of the reaction is the protonation of a zwitterionic intermediate by the catalyst. This represents a rare case in which a thiourea compound functions as an asymmetric Bronsted acid catalyst.
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