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Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines.

ABSTRACT: Chelated ketone enolates are excellent nucleophiles for allylic alkylations. Electron-withdrawing groups on the allyl moiety allow subsequent intramolecular Michael additions giving rise to piperidines with up to five stereogenic centers.

SUBMITTER: Prudel C

PROVIDER: S-EPMC7079034 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines.

Prudel Cynthia C Huwig Kai K Kazmaier Uli U

Chemistry (Weinheim an der Bergstrasse, Germany) 20200221 14

Chelated ketone enolates are excellent nucleophiles for allylic alkylations. Electron-withdrawing groups on the allyl moiety allow subsequent intramolecular Michael additions giving rise to piperidines with up to five stereogenic centers. ...[more]

PMID: 31943413

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