Kinetic Resolution of Secondary Alcohols by NHC-Catalyzed Oxidative Esterification

Abstract

Kinetic resolution of racemic secondary alcohols by oxidative esterification using carbene catalysis is described. Good to moderate selectivity has been achieved. N-Heterocyclic carbenes (NHCs) were systematically varied and several aldehydes were included in this study as acyl donors. As an oxidant, a readily available bisquinone-type system was used.

Key words

carbene catalysis - kinetic resolution - oxidative esterification - secondary alcohols - acylazolium ions

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15

Scheidt and co-workers reported the desymmetrization of meso-diols using oxidative carbene catalysis; see ref. 8a.

18

The absolute configuration of the major enantiomer of 15a formed using catalyst 8 was determined by comparing the HPLC retention time with that of an authentic sample.