Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent.
[reaction: see text] Zinc-complexed methylene ammonium ylides are formed from tertiary amines and the Simmons-Smith reagent. These stable entities can be activated with n-BuLi to allow reactions typical of ammonium ylides such as [2,3] rearrangements. In the case of oxazolidine 12, ylide formation, activation, and subsequent [2,3] rearrangement was highly efficient and occurred with very high diastereoselectivity.
Aggarwal
Varinder K
VK
Department of Chemistry, University of Bristol, Cantock's Close, Bristol, UK. v.aggarwal@bristol.ac.uk
Fang
Guang Yu
GY
Charmant
Jonathan P H
JP
Meek
Graham
G