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Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

ABSTRACT: The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

SUBMITTER: Shuler SA

PROVIDER: S-EPMC5395365 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Shuler Scott A SA Yin Guoyin G Krause Sarah B SB Vesper Caroline M CM Watson Donald A DA

Journal of the American Chemical Society 20161018 42

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway. ...[more]

PMID: 27754648

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