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Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications.

ABSTRACT: We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine?B, and the indolinoquinoline rings of communesin?B are reported.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3714863 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications.

Trost Barry M BM Zhang Yong Y

Chemistry (Weinheim an der Bergstrasse, Germany) 20110202 10

We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids suc ...[more]

PMID: 21290436

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