4.8 Article

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 42, Pages 13830-13833

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08932

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Funding

  1. University of Delaware (UD)
  2. NIH [P20 GM104316, NSF CHE0421224, CHE1229234, CHE0840401, NIH P20GM104316, P30GM110758, S10RR026962, S10OD016267]

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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.

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