Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 6, Pages 1998-2001Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b12185
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Funding
- Vanderbilt University Summer Research Program
- National Institute of General Medical Sciences [NIH GM 084333]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM084333] Funding Source: NIH RePORTER
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The enantioselective desymnitrization of carboxylic acids by chiral Bronsted base-catalysis is reported, leading to bridged bicyclic lactones with up to 94% ee. Crystallographic analysis of a substrate-catalyst complex suggests an origin of stereocontrol, retniniscent of functional Bronsted bases in biological Settings, and enabled reaction optimization. The products contain an all-carbon qiiaternary stereocenter and can be-derivatized to functionalized cyclopentanes.
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