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Asymmetric Aza‐MoritaBaylisHillman Reaction of N ‐Sulfonated Imines with Methyl Vinyl Ketone Catalyzed by Chiral Phosphine Lewis Bases Bearing Perfluoroalkanes as “Pony Tails”
Author(s) -
Shi Min,
Chen LianHui,
Teng WenDong
Publication year - 2005
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.200505123
Subject(s) - methyl vinyl ketone , chemistry , lewis acids and bases , ketone , adduct , phosphine , medicinal chemistry , catalysis , organic chemistry , silylation
In the aza‐Morita–BaylisHillman 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(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silyl]‐2′‐(diphenylphosphanyl)‐[1,1′]binaphthalenyl‐2‐ol LB2 and ( R )‐(−)‐6,6′‐(3,3,4,4,5, 5,6,6,7,7,8,8,8‐tridecafluorooctyl) ‐2′‐(diphenylphosphanyl)‐[1,1′]binaphthalenyl‐2‐ol LB3 bearing two perfluoroalkane chains at 6,6′‐positions of the naphthalene framework, the corresponding adducts could be obtained in good yields with good to high ee (52–95% ee) at room temperature (15 °C) or low temperature (−20 °C) in THF, respectively. LB3 is more effective in this reaction than the previously reported original chiral phosphine Lewis base ( R )‐(−)‐2′‐diphenylphosphanyl‐[1,1′]binaphthalenyl‐2‐ol LB1 .