Sequential Double α-Arylation of N-Allylureas by Asymmetric Deprotonation and N→ C Aryl Migration

DJ Tetlow, U Hennecke, J Raftery, MJ Waring…

Index: Clayden, Jonathan; Farnaby, William; Grainger, Damian M.; Hennecke, Ulrich; Mancinelli, Michele; Tetlow, Daniel J.; Hillier, Ian H.; Vincent, Mark A. Journal of the American Chemical Society, 2009 , vol. 131, # 10 p. 3410 - 3411

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Citation Number: 32

Abstract

On lithiation with lithium amides, N-allyl-N′-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1, 1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.