The Enantioselective Michael Addition of Thiols to Cycloalkenones by Using (2S, 4S)-2-Anilinomethyl-1-ethyl-4-hydroxypyrrolidine as Chiral Catalyst
- 1 October 1982
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 55 (10) , 3277-3282
- https://doi.org/10.1246/bcsj.55.3277
Abstract
Catalytic asymmetric addition of thiols to 2-cycloalkenone was studied by using the chiral amino alcohols, derived from L-hydroxyproline or (S)-proline, as base catalysts. Detailed investigation was carried out on the effects of the structure of the catalyst, the reaction medium, the temperature, and the concentration on the enantioselectivity. Good optical yields (47–88%) were achieved by the reaction of arenethiols and 2-cyclohexen-1-one in toluene at −5 °C, by using the catalyst (2S, 4S)-2-anilinomethyl-1-ethyl-4-hydroxypyrrolidine.Keywords
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