Title

Catalytic parallel kinetic resolution under homogeneous conditions

Document Type

Article

Publication Title

Journal of Organic Chemistry

Publication Date

7-16-2010

Abstract

(Figure Presented) Two complementary chiral catalysts, the phosphine 8d and the DMAP-derived ent-23b, are used simultaneously to selectively activate a mixture of two different achiral anhydrides as acyl donors under homogeneous conditions. The resulting activated intermediates 25 and 26 react with the racemic benzylic alcohol 5 to form enantioenriched esters (R)-24 and (S)-17 by fully catalytic parallel kinetic resolution (PKR). The aroyl ester (R)-24 is obtained with near-ideal enantioselectivity for the PKR process, but (S)-17 is contaminated by ca. 8% of the minor enantiomer (R)-17 resulting from a second pathway via formation of mixed anhydride 27 and its activation by 8d. © 2010 American Chemical Society.

Volume

75

Issue

14

First Page

4674

Last Page

4685

DOI

10.1021/jo100695z

ISSN

00223263

E-ISSN

15206904

PubMed ID

20557113

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