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Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

ABSTRACT: Au(I) in combination with AgOTf enables the unprecedented direct and ?-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles.

SUBMITTER: Palo-Nieto C

PROVIDER: S-EPMC5951607 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.

Palo-Nieto Carlos C Sau Abhijit A Galan M Carmen MC

Journal of the American Chemical Society 20170928 40

Au(I) in combination with AgOTf enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles. ...[more]

PMID: 28934850

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