The preparation of optically pure 3-hydroxyalkanoic acid. The enantioface-differentiating hydrogenation of the C= O double bond with modified Raney nickel. XXXVII.

M Nakahata, M Imaida, H Ozaki, T Harada…

Index: Nakahata, Masaaki; Imaida, Motomasa; Ozaki, Hiroshi; Harada, Tadao; Tai, Akira Bulletin of the Chemical Society of Japan, 1982 ,  vol. 55,  # 7  p. 2186 - 2189

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Citation Number: 95

Abstract

The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH 3 (CH 2) n COCH 2 COOCH 3, n= 0, 6, 8, 10, 12) over the (R, R)-tartaric acid–NaBr–modified Raney nickel catalyst ((R, R)-TA–NaBr–MRNi) gave methyl (R)-3-hydroxyalkanoate (CH 3 (CH 2) n CH (OH) CH 2 COOCH 3, n= 0, 6, 8, 10, 12) in an average optical yield of 85%. After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid ...