Stereoselective Synthesis of Allylic Amines by One-Pot Tandem Reaction of Acetylenic Sulfone, Grignard Reagent, and N-Tosylimine

Abstract

Polysubstituted allylic amines were regio- and stereoselectively synthesized by a one-pot tandem reaction of Cu(I)-catalyzed carbomagnesiation of acetylenic sulfones and its further reaction with N-tosylimine.

Keywords:

• Acetylenic sulfone
• allylic amine
• carbomagnesiation
• Grignard reagent
• N-tosylimine

ACKNOWLEDGMENTS

The authors are grateful to the National Natural Science Foundation of China (No. 20672001 and 20772001) and the Anhui Education Department (No. TD200707) for financial support of this research. We are also grateful to Jiping Hu, Gaosheng Yang, Baohui Du, and Yun Wei for their helpful assistance.

Notes

^a Isolated yield based on the acetylenic sulfone used. The ratio of Z/E was determined by 300 MHz ¹H NMR spectra of the unpurified reaction mixture.