Anionic O --> alpha- and beta-vinyl carbamoyl translocation of 2-(O-carbamoyl) stilbenes.
[reaction: see text] New anionic oxygen to alpha- and beta-vinyl carbamoyl migration reactions, 17a and 26a-c --> 18 and 30a-c, proceed under LDA-mediated conditions leading stereoselectively to highly substituted stilbenes bearing electron-donating and -withdrawing substituents. Compounds 17a and 26a-c are prepared by combination of efficient, directed ortho metalation, Sonogashira, and Suzuki-Miyaura cross-coupling procedures.
Reed
Mark A
MA
Department of Chemistry, Queen's University, Kingston, ON, K7L 3N6, Canada.
Chang
Michelle T
MT
Snieckus
Victor
V