Palladium‐Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.

Yuan, Qianjia; Sigman, Matthew S.

In this report, a palladium‐catalyzed redox‐relay Heck process to access optically active alkenylated α,β‐unsaturated lactams is described. Under mild reaction conditions, electron‐deficient alkenyl triflates and electron‐rich alkenyl iodonium salts undergo enantioselective and site‐selective coupling with enelactams to deliver the products in high yields and excellent enantioselectivities. Furthermore, the products allow facile access to natural products such as ( )‐calvine and ( )‐2‐epicalvine in addition to the bioactive molecule aza‐goniothalamin.

ALKENYLATION; NATURAL products; IODONIUM salts; LACTAMS; HECK reaction

Chemistry - A European Journal, 2019, Vol 25, Issue 46, p10823

0947-6539

Academic Journal

10.1002/chem.201902813