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Dendritic Chiral Phosphine Lewis Bases-Catalyzed Asymmetric Aza-Morita–Baylis–Hillman Reaction of N-Sulfonated Imines with Activated Olefins

✍ Scribed by Ying-hao Liu; Min Shi

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
242 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

A series of polyether dendritic chiral phosphine Lewis bases was synthesized, and successfully applied to the asymmetric aza‐Morita–Baylis–Hillman reaction of N‐sulfonated imines (N‐arylmethylidene‐4‐methylbenzenesulfonamides) with methyl vinyl ketone (MVK), ethyl vinyl ketone (EVK), and acrolein to give the adducts in good to excellent yields along with up to 97 % ee, which are more effective than our previously reported original chiral phosphine Lewis bases. In addition, the dendrimer‐supported chiral phosphine Lewis bases can be easily recovered and reused.

📜 SIMILAR VOLUMES

Asymmetric Aza-MoritaBaylisHillman React
Asymmetric Aza-MoritaBaylisHillman Reaction of N-Sulfonated Imines with Methyl Vinyl Ketone Catalyzed by Chiral Phosphine Lewis Bases Bearing Perfluoroalkanes as “Pony Tails”
✍ Min Shi; Lian-Hui Chen; Wen-Dong Teng 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 174 KB 👁 2 views

## Abstract In the aza‐Morita–BaylisHillman reaction of __N__‐sulfonated imines (__N__‐arylmethylidene‐4‐methylbenzenesulfonamides and others) with methyl vinyl ketone (MVK), we found that in the presence of a catalytic amount of the chiral phosphine Lewis bases (__R__)‐(−)‐6,6′‐bis[tris(3,3,4,4,5