Anionic O --> alpha- and beta-vinyl carbamoyl translocation of 2-(O-carbamoyl) stilbenes

Organic Letters
Mark A ReedVictor Snieckus

Abstract

[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.

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Citations

Jul 8, 2008·Chembiochem : a European Journal of Chemical Biology·Anne-Sophie RebstockDavid L Selwood
May 9, 2019·Chemical Society Reviews·Marcus Korb, Heinrich Lang
Oct 8, 2020·Angewandte Chemie·Johannes H HarenbergPaul Knochel
Feb 20, 2009·Journal of the American Chemical Society·Thomas TricotetDonal F O'Shea
Apr 5, 2018·Organic Letters·Claudia FebereroRoberto Sanz
Sep 9, 2020·The Journal of Organic Chemistry·Claudia FebereroRoberto Sanz

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