Issue 11, 2003

Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate

Abstract

In the aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone (MVK) promoted by chiral phosphine Lewis base: (R)-2′-diphenylphosphanyl-[1,1′]binaphthalenyl-2-ol (10 mol%), the aza-Baylis–Hillman adducts 1 were obtained in good yields with high ee (70–94% ee) at −30 °C in THF. In CH2Cl2 upon heating at 40 °C, the aza-Baylis–Hillman reaction of N-sulfonated imines with phenyl acrylate gave the adducts 2 in high yields (60–97%) with moderate ee (52–77%).

Graphical abstract: Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate

Supplementary files

Article information

Article type
Communication
Submitted
17 Feb 2003
Accepted
09 Apr 2003
First published
06 May 2003

Chem. Commun., 2003, 1310-1311

Chiral phosphine Lewis base catalyzed asymmetric aza-Baylis–Hillman reaction of N-sulfonated imines with methyl vinyl ketone and phenyl acrylate

M. Shi and L. Chen, Chem. Commun., 2003, 1310 DOI: 10.1039/B301863F

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