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Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.

ABSTRACT: Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched alpha-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening.

SUBMITTER: Petersen KS

PROVIDER: S-EPMC2628291 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters.

Petersen Kimberly S KS Posner Gary H GH

Organic letters 20080924 20

Efficient and enantiocontrolled synthesis of gamma-hydroxy-alpha,beta-unsaturated sulfones and esters are reported through the reaction of enantioenriched alpha-selenyl aldehydes with EWG-stabilized carbanions and then a one-pot selenide oxidation, in situ epoxide formation, and final in situ epoxide opening. ...[more]

PMID: 18811178

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Asymmetric, organocatalytic, three-step synthesis of alpha-hydroxy-(E)-beta,gamma-unsaturated esters.

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