Enantioface-differentiating Reactions Using (2S,2′S)-2-Hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines as Chiral Ligands. Addition of Lithium Derivatives of Methyl Phenyl Sulfide, Acetonitrile, N-Nitrosodimethylamine, and 2-Methylthiothiazoline to Aldehydes
- 1 November 1979
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 52 (11) , 3371-3376
- https://doi.org/10.1246/bcsj.52.3371
Abstract
Optically active oxiranes, β-hydroxy nitrile, β-Hiydroxy N-nitrosoamine, and thiirane were obtained (up to 72% optical purity) by the enantioface-differentiating addition of lithium derivatives of methyl phenyl sulfide, acetonitrile, N-nitrosodimethylamine, and 2-methylthiothiazoline to aldehydes using (2S,2′S)-2-hydroxymethyl-1-[(1-alkyl-2-pyrrolidinyl)methyl]pyrrolidines (1a–f) as chiral ligands. Optical purity of the products depended greatly on the reaction medium (dimethoxymethane or dimethyl ether gave the best results) and the structure of pyrrolidine moieties of 1a–f.)Keywords
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