Gold(I)-catalyzed highly regio- and stereoselective decarboxylative amination of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement in water

Dong Xing; Dan Yang

doi:10.1021/ol100056f

Gold(I)-catalyzed highly regio- and stereoselective decarboxylative amination of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement in water

Org Lett. 2010 Mar 5;12(5):1068-71. doi: 10.1021/ol100056f.

Authors

Dong Xing¹, Dan Yang

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

PMID: 20143843
DOI: 10.1021/ol100056f

Abstract

A gold(I)-catalyzed decarboxylative amination of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement has been developed. A variety of substituted N-tosyl allylic amines were obtained in good yield, excellent regioselectivity, and high to excellent stereoselectivity. This transformation could be performed either in H(2)O or in one pot directly from allylic alcohols and therefore represents an efficient and environmentally benign protocol for the synthesis of N-tosyl allylic amines.