Asymmetric Hydrogenation via Capture of Active Intermediates Generated from Aza-Pinacol Rearrangement

CB Yu, WX Huang, L Shi, MW Chen…

Index: Geary, Laina M.; Chen, Te-Yu; Montgomery, T. Patrick; Krische, Michael J. Journal of the American Chemical Society, 2014 , vol. 136, # 16 p. 5920 - 5922

Full Text: HTML

Citation Number: 6

Abstract

An efficient palladium-catalyzed asymmetric hydrogenation via capture of an active intermediate generated in situ from acid-catalyzed aza-Pinacol rearrangement has been successfully developed, providing efficient access to chiral exocyclic amines with up to 98% ee. Three-, four-, and five-membered cyclic N-sulfonyl amino alcohols are viable substrates. This study opens a new window to the application of asymmetric hydrogenation.