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Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

ABSTRACT: Through the use of an amino acid based imidazole catalyst, a regiodivergent silylation of chiral diols in cases where there is not a significant steric and electronic difference between the regioisotopic hydroxyl groups has been developed. This transformation allows for the conversion of racemic diols into regioisomeric, enantiomerically enriched, monosilylated products. The utility of this process is highlighted in the efficient enantioselective preparation of a useful synthetic intermediate and the natural product, sapinofuranone A.

SUBMITTER: Rodrigo JM

PROVIDER: S-EPMC3146572 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

Rodrigo Jason M JM Zhao Yu Y Hoveyda Amir H AH Snapper Marc L ML

Organic letters 20110628 15

Through the use of an amino acid based imidazole catalyst, a regiodivergent silylation of chiral diols in cases where there is not a significant steric and electronic difference between the regioisotopic hydroxyl groups has been developed. This transformation allows for the conversion of racemic diols into regioisomeric, enantiomerically enriched, monosilylated products. The utility of this process is highlighted in the efficient enantioselective preparation of a useful synthetic intermediate an ...[more]

PMID: 21711005

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