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Catalytic nucleophilic glyoxylation of aldehydes.

ABSTRACT: Beta-silyloxy-alpha-keto esters are prepared through a cyanide-catalyzed benzoin-type reaction with silyl glyoxylates and aldehydes. The products undergo a dynamic kinetic resolution to provide enantioenriched orthogonally protected alcohols and can be converted to the corresponding beta-silyloxy-alpha-amino esters.

SUBMITTER: Steward KM

PROVIDER: S-EPMC2890213 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Catalytic nucleophilic glyoxylation of aldehydes.

Steward Kimberly M KM Johnson Jeffrey S JS

Organic letters 20100601 12

Beta-silyloxy-alpha-keto esters are prepared through a cyanide-catalyzed benzoin-type reaction with silyl glyoxylates and aldehydes. The products undergo a dynamic kinetic resolution to provide enantioenriched orthogonally protected alcohols and can be converted to the corresponding beta-silyloxy-alpha-amino esters. ...[more]

PMID: 20481613

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