Gold(I)-Catalyzed Highly Regio- and Stereoselective Decarboxylative Amination of Allylic N-Tosylcarbamates via Base-Induced Aza-Claisen Rearrangement in Water

Dong Xing and Dan Yang*

*Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China, Email: yangdanhku.hk

D. Xing, D. Yang, Org. Lett., 2010, 12, 1068-1071.

DOI: 10.1021/ol100056f

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Abstract

A gold(I)-catalyzed decarboxylative amination of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement in H₂O allows the synthesis of substituted N-tosyl allylic amines in good yield, regioselectivity, and stereoselectivity. This transformation represents an efficient and environmentally benign protocol for the synthesis of N-tosyl allylic amines.

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Key Words

Allylic Amines, Sulfonamides, Green Chemistry, Claisen Rearrangement

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ID: J54-Y2010-0670