Article

Asymmetric hydrogenation of alpha-hydroxy ketones catalyzed by MsDPEN-Cp*Ir(III) complex.

Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Organic Letters (impact factor: 5.86). 07/2007; 9(13):2565-7. DOI:10.1021/ol070964w pp.2565-7
Source: PubMed

ABSTRACT Asymmetric hydrogenation of a series of alpha-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.

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Keywords

1-aryl-1,2-ethanediols
 
Asymmetric hydrogenation
 
enantioselectivity
 
substrate-to-catalyst molar ratio
 

Takeshi Ohkuma