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Axially Chiral Phosphine‐Oxazoline Ligands in Silver(I)‐ Catalyzed Asymmetric Mannich Reaction of Aldimines with Trimethylsiloxyfuran
Author(s) -
Deng HongPing,
Wei Yin,
Shi Min
Publication year - 2009
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.200900550
Subject(s) - aldimine , chemistry , oxazoline , phosphine , catalysis , medicinal chemistry , diastereomer , organic chemistry , mannich reaction , trifluoroacetic acid , ligand (biochemistry) , chiral ligand , yield (engineering) , enantioselective synthesis , biochemistry , materials science , receptor , metallurgy
A new asymmetric catalytic system for the Mannich reaction of aldimines with trimethylsiloxyfuran is described. The combination of an axially chiral phosphine‐oxazoline ligand ( S )‐2‐[( R )‐2′‐(diphenylphosphino)‐1,1′‐binaphthyl‐2‐yl]‐4‐phenyl‐4,5‐dihydrooxazole with silver acetate and 2,2,2‐trifluoroacetic acid is a very effective catalytic system in the asymmetric Mannich reaction of various aldimines with trimethylsiloxyfuran in dichloromethane at −78 °C, affording the corresponding adducts in up to 99% yield, 99:1 ( dr ) and 99% ee (major diastereoisomer) under mild conditions.