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Visible Light-Promoted Enantioselective Aerobic Hydroxylation of β-Ketocarbonyls by Chiral Primary Amine Catalysis
ACS Catalysis ( IF 12.9 ) Pub Date : 2023-05-19 , DOI: 10.1021/acscatal.3c01477
Mao Cai, Kaini Xu, Haoyuan Jia, Long Zhang, Xueling Mi, Sanzhong Luo

Highly effective and stereoselective enamine-singlet oxygen coupling was achieved by synergistic chiral primary amine and photocatalysis in hexafluoroisopropanol. The current enamine catalysis enables α-hydroxylation of β-ketocarbonyls with good yields and high enantioselectivity across a broad range of substrates. Mechanistic studies revealed a direct participation of solvents in the critical enamine coupling step, and a solvent-1O2 H-bonding mode was invoked to account for the dramatic solvent effect.

中文翻译:

手性伯胺催化可见光促进β-酮羰基的对映选择性好氧羟基化

通过在六氟异丙醇中协同手性伯胺和光催化,实现了高效和立体选择性的烯胺-单线态氧偶联。当前的烯胺催化能够实现β-酮基羰基的α-羟基化,在广泛的底物范围内具有良好的产率和高对映选择性。机理研究揭示了溶剂直接参与关键的烯胺偶联步骤,并调用了溶剂- 1 O 2 H-键合模式来解释显着的溶剂效应。
更新日期:2023-05-19
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