The aza-[2,3]-Wittig sigmatropic rearrangement of Z(C)-alkenes can be
achieved through the use of a trimethylsilyl anion stabilising group.
The major diastereoisomer complements previous results aid allows acce
ss to each diastereoisomer of the homoallylic amine products. A transi
tion state model is described which accounts for the diminished diaste
reoselection compared to E-alkyl substrates. (C) 1998 Elsevier Science
Ltd. All rights reserved.