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Asymmetric Hydrogenation of α‐Keto Phosphonates with Chiral Palladium Catalysts
Author(s) -
Goulioukitaliya S.,
Bondarenko Grigorii N.,
Bogdanov Alexei V.,
Gavrilov Konstantin N.,
Beletskaya Irina P.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800943
Subject(s) - chemistry , palladium , catalysis , aryl , hydrogen , asymmetric hydrogenation , organic chemistry , carbon fibers , medicinal chemistry , atmospheric pressure , polymer chemistry , enantioselective synthesis , alkyl , materials science , composite number , composite material , oceanography , geology
Under atmospheric hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and ( R )‐MeO‐BIPHEP in 2,2,2‐trifluoroethanol promoted the asymmetric hydrogenation of diisopropyl α‐keto phosphonates 1 to afford the corresponding α‐hydroxy phosphonates 2 in excellent yields and with a moderate enantioselectivities of up to 55 % ee . Racemic α‐aryl‐α‐hydroxy phosphonates can be prepared by using palladium on carbon as the catalyst. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)