The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Asymmetrically Modified Raney Nickel. XXXVIII. The Hydrogenation of Methyl Ketones to Optically Active Secondary Alcohols
- 1 June 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 57 (6) , 1518-1521
- https://doi.org/10.1246/bcsj.57.1518
Abstract
The enantioface-differentiating (asymmetric) hydrogenation of various methyl ketones (R–COCH3) was carried out over the Raney nickel catalyst modified with (R,R)-tartaric acid and sodium bromide. The presence of an appreciable amount of carboxylic acid in the reaction system was indispensable for a high optical yield. The highest optical yield (74%) was obtained in the hydrogenation of 3,3-dimethyl-2-butanone in the presence of pivalic acid.Keywords
This publication has 11 references indexed in Scilit:
- Stereochemical Investigation on Asymmetrically Modified Raney Nickel Catalyst. Mode of Interaction between Modifying Reagent and Substrate in the Enantioface-differentiating ProcessBulletin of the Chemical Society of Japan, 1983
- The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.Bulletin of the Chemical Society of Japan, 1982
- The Enantioface-differentiating (Asymmetric) Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVI. The Development of Modified Nickel Catalysts with High Enantioface-differentiating AbilitiesBulletin of the Chemical Society of Japan, 1981
- Stereochemical Studies of the Hydrogenation with an Asymmetrically Modified Raney Nickel Catalyst. The Hydrogenation of AcetylacetoneBulletin of the Chemical Society of Japan, 1981
- The Stereo-differentiating (Asymmetric) Hydrogenation of the C=O Double Bond with a Modified Nickel Catalyst. XXXV. A Facile Method for the Preparation of Optically Pure β-DiolsBulletin of the Chemical Society of Japan, 1980
- The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Asymmetrically Modified Raney Nickel. XXXIII. The Preparation of (R)- and (S)-1,3-Butanediol from 4-Hydroxy-2-butanoneBulletin of the Chemical Society of Japan, 1980
- .alpha. Anions of carboxylic acids. II. Formation and alkylation of .alpha.-metalated aliphatic acidsThe Journal of Organic Chemistry, 1972
- Methods of Asymmetric Synthesis—Enantioselective Catalytic HydrogenationAngewandte Chemie International Edition in English, 1971
- CVII.—Investigations on the dependence of rotatory power on chemical constitution. Part VI. The optical rotatory power of methyl-tert.-butyl-, methylbenzyl-, methylphenylethyl- and methyl-α-naphthyl-carbinolsJournal of the Chemical Society, Transactions, 1914
- VII.—Investigations on the dependence of rotatory power on chemical constitution. Part I. The rotations of the simplest secondary alcohols of the fatty seriesJournal of the Chemical Society, Transactions, 1911