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Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

ABSTRACT: A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N-protecting group is particularly important for achieving high regio- and diastereoselectivity. Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3488305 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Trost Barry M BM Zhang Yong Y

Chemistry (Weinheim an der Bergstrasse, Germany) 20100101 1

A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N-protecting group is particularly important for achieving high regio- and diastereoselectivity. Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utilit ...[more]

PMID: 20013766

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