Asymmetric [2,3]-sigmatropic rearrangement of allylic ammonium ylides

Jan Blid; Olaf Panknin; Peter Somfai

doi:10.1021/ja0510562

Asymmetric [2,3]-sigmatropic rearrangement of allylic ammonium ylides

J Am Chem Soc. 2005 Jul 6;127(26):9352-3. doi: 10.1021/ja0510562.

Authors

Jan Blid¹, Olaf Panknin, Peter Somfai

Affiliation

¹ Organic Chemistry, KTH Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden.

PMID: 15984846
DOI: 10.1021/ja0510562

Abstract

An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprotonation and rearrangement.