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Catalytic Enantiodifferentiating Hydrogenation with Commercial Nickel Powders Chirally Modified by Tartaric Acid and Sodium Bromide
Author(s) -
Osawa Tsutomu,
Kizawa Tomoko,
Takano Fumika,
Ikeda Shinji,
Kitamura Takayuki,
Inoue Yoshihisa,
Borovkov Victor
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300727
Subject(s) - nickel , enantiopure drug , tartaric acid , catalysis , bromide , asymmetric hydrogenation , chemistry , enantioselective synthesis , organic chemistry , citric acid
The chirally modified nickel catalysts for the enantiodifferentiating hydrogenation of β‐ketoesters are prepared conventionally by immersing hydrogen‐activated metallic nickel into an aqueous solution of enantiopure tartaric acid, in which the preactivation of nickel is essential. Herein, we revealed that even commercially available nickel powders without any pretreatment can catalyze the enantiodifferentiating hydrogenation of β‐ketoesters to give the corresponding β‐hydroxyesters in quantitative yield and high enantioselectivity (up to 91 %) under optimized conditions. The immediate use of commercially available nickel powders and the reproducible high chemical and optical yields not only expand the scope of heterogeneous asymmetric catalysis but also pave the way for the practical application and industrial use of chirally modified nickel catalysts.