Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

• DOI: 10.1021/jacs.6b08932
• Publication Date: 2016-10-18T21:03:20Z
• Authors: Scott A. Shuler; Guoyin Yin; Sarah B. Krause; Caroline M. Vesper; Donald A. Watson
• Keywords: 01 natural sciences; 0104 chemical sciences

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.