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Enantioselective Desymmetrization of Diesters

Jennifer Wilent and Kimberly S. Petersen*

*Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina 27402, United States, Email: kspetersuncg.edu

J. Wilent, K. S. Petersen, J. Org. Chem., 2014, 79, 2303-2307.

DOI: 10.1021/jo402853v (free Supporting Information)



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Abstract

A desymmetrization of prochiral diesters with a chiral phosphoric acid catalyst produces highly enantioenriched lactones in excellent yield. Various substitution patterns are tolerated, many of which result in the generation of an enantioenriched all-carbon quaternary center. Manipulation of the lactone products to useful small building blocks is also described.

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Key Words

Lactones


ID: J42-Y2014