期刊
ACS CATALYSIS
卷 13, 期 4, 页码 2240-2249出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c05484
关键词
oxa-Pictet-Spengler reaction; asymmetric catalysis; dual catalysis; anion-binding catalysis; oxocarbenium ions; kinetic isotope effects; DFT calculations
The enantioselective oxa-Pictet-Spengler reactions of tryptophol with aldehydes were successfully conducted under weakly acidic conditions using a combination of indoline HCl salt and bisthiourea compound as catalysts. Mechanistic investigations determined the roles of both catalysts and confirmed the involvement of oxocarbenium ion intermediates, ruling out alternative scenarios. A stereochemical model derived from density functional theory calculations provided the basis for the development of a highly enantioselective stereodivergent variant with racemic tryptophol derivatives.
Enantioselective oxa-Pictet-Spengler reactions of tryptophol with aldehydes proceed under weakly acidic conditions utilizing a combination of two catalysts, an indoline HCl salt and a bisthiourea compound. Mechanistic investigations revealed the roles of both catalysts and confirmed the involvement of oxocarbenium ion intermediates, ruling out alternative scenarios. A stereochemical model was derived from density functional theory calculations, which provided the basis for the development of a highly enantioselective stereodivergent variant with racemic tryptophol derivatives.
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