Reaction of N-Tosylated Imines with α,β-Acetylenic Ketones via Organozinc Species

Abstract

A new procedure for stereoselective synthesis of trisubstituted alkenes by an one-pot, three-component reaction of N-tosylated imines with α,β-acetylenic ketones and organozinc species CF₃COOZnEt was described. This reaction system provides β-branched Morita–Baylis–Hillman adducts with excellent yields in absence of any catalyst.

Keywords:

• α,β-Acetylenic ketones
• CF₃COOZnEt
• N-tosylated imines
• trisubstituted alkenes

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (20572104) and the program of New Century Excellent Talents in University (NCET) (060551) for financial support.

Notes

^a Yields after purification by column chromatography.

^b Performed in Et₂O.

^c Performed in THF.

^d Performed at 0 °C.