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Dendritic Chiral Phosphine Lewis Bases‐Catalyzed Asymmetric Aza‐Morita–Baylis–Hillman Reaction of N ‐Sulfonated Imines with Activated Olefins
Author(s) -
Liu Yinghao,
Shi Min
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700338
Subject(s) - methyl vinyl ketone , chemistry , phosphine , lewis acids and bases , baylis–hillman reaction , ketone , adduct , acrolein , catalysis , organocatalysis , organic chemistry , asymmetric induction , diastereomer , enantioselective synthesis
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.