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N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

ABSTRACT: Asymmetric hydration of alpha,alpha-dichloro aldehydes and alpha-halo enals via a NHC-catalyzed redox process to yield enantioenriched alpha-chloro and alpha-fluoro carboxylic acids is described herein. The developed reaction allows for installation of an alpha-deuterium to give rise to enantioenriched alpha-deutero alpha-halo acids using D(2)O as the deuteron source.

SUBMITTER: Vora HU 

PROVIDER: S-EPMC2839412 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

Vora Harit U HU   Rovis Tomislav T  

Journal of the American Chemical Society 20100301 9

Asymmetric hydration of alpha,alpha-dichloro aldehydes and alpha-halo enals via a NHC-catalyzed redox process to yield enantioenriched alpha-chloro and alpha-fluoro carboxylic acids is described herein. The developed reaction allows for installation of an alpha-deuterium to give rise to enantioenriched alpha-deutero alpha-halo acids using D(2)O as the deuteron source. ...[more]

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