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Org Lett. 2010 Mar 5;12(5):1068-71. 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.

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

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.

PMID:
20143843
DOI:
10.1021/ol100056f

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