Asymmetric Hydrogenation of α-Hydroxy Ketones Catalyzed by MsDPEN−CpIr(III) Complex

Asymmetric hydrogenation of a series of α-hydroxy aromatic ketones in methanol catalyzed by Cp*Ir(OTf)(MsDPEN) (MsDPEN = N-(methanesulfonyl)-1,2-diphenylethylenediamine) affords the 1-aryl-1,2-ethanediols in up to 99% ee. The reaction can be conducted with a substrate-to-catalyst molar ratio as high...

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Bibliographic Details
Published in:Organic letters 2007-06, Vol.9 (13), p.2565-2567
Main Authors: Ohkuma, Takeshi, Utsumi, Noriyuki, Watanabe, Masahito, Tsutsumi, Kunihiko, Arai, Noriyoshi, Murata, Kunihiko
Format: Article
Language:English
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Summary:Asymmetric hydrogenation of a series of α-hydroxy aromatic ketones in methanol catalyzed by Cp*Ir(OTf)(MsDPEN) (MsDPEN = N-(methanesulfonyl)-1,2-diphenylethylenediamine) affords the 1-aryl-1,2-ethanediols in up to 99% ee. The reaction can be conducted with a substrate-to-catalyst molar ratio as high as 6000 under 10 atm of H2. 1-Hydroxy-2-propanone is also hydrogenated with high enantioselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070964w