Sequential double α-arylation of N-allylureas by asymmetric deprotonation and N→C aryl migration.

Daniel J Tetlow, Ulrich Hennecke, James Raftery, Michael J Waring, David S Clarke, Jonathan Clayden

Index: Org. Lett. 12(23) , 5442-5, (2010)

Full Text: HTML

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.