Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 17, Pages 7321-7324Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3027086
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Funding
- Alfred P. Sloan Foundation
- LaMattina Fellowship
- NSF [CHE-1150393, DBI-0619576]
- NIGMS [R01GM087581]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1150393] Funding Source: National Science Foundation
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This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.
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