Asymmetric Hydrogenation of Oximes Synergistically Assisted by Lewis and Brønsted Acids

• DOI: 10.1021/jacs.2c07506
• Publication Date: 2022-09-27T15:36:25Z
• Authors: Fangyuan Wang; Yu Chen; Peiyuan Yu; Gen-Qiang Chen; Xumu Zhang
• Keywords: Brønsted–Lowry acid–base theory; Reactivity; Bond cleavage; Asymmetric hydrogenation

Due to their low reactivity, difficult enantiocontrol, and proneness N–O bond cleavage, the catalytic asymmetric hydrogenation of oximes hydroxylamines has remained a significant challenge. Herein, Lewis Brønsted acid cooperation strategy was established for oximes, providing corresponding with up 95% yield 96% ee. Addition crucial obtain high conversion enantioselectivity. Mechanistic investigations indicates that thiourea fragment ligand, (In(OTf)3 or Zn(OAc)2), as well (l-CSA) played vital roles in control reactivity enantioselectivity reaction. In addition, synthetic elaboration this transformation demonstrated by gram scale experiment retention