Stereoselective synthesis of optically active alpha-hydroxy ketones and anti-1,2-diols via asymmetric transfer hydrogenation of unsymmetrically substituted 1,2-diketones.
[reaction: see text] A well-defined chiral Ru catalyst RuCl(N-(p-toluenesulfonyl)-1, 2-diphenylethylenediamine)(eta(6)-arene) effectively promotes asymmetric transfer hydrogenation of 1-aryl-1,2-propanedione with HCOOH/N(C(2)H(5))(3), leading preferentially to optically active 1-aryl-2-hydroxy-1-propanone with up to 99% ee and 89% yield at 10 degrees C. The reaction at 40 degrees C gives anti-1-aryl-1, 2-propanediol with up to 95% ee and 78% yield. This is a highly efficient procedure for the synthesis of optically active anti-diols.
Koike
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T
Graduate School of Science and Engineering, Tokyo Institute of Technology and CREST, Japan Science and Technology Corporation, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
Murata
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K
Ikariya
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T
D002384:Catalysis; D006018:Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D017975:Ruthenium Compounds; D013237:Stereoisomerism
D006018:Glycols; D007659:Ketones; D017975:Ruthenium Compounds