对映选择合成
磷酸
氧化还原
光催化
化学
组合化学
级联
级联反应
有机化学
催化作用
色谱法
作者
Qipeng Chen,Yuanli Zhu,Xujing Shi,Renfu Huang,Chuang Jiang,Kun Zhang,Guohua Li
出处
期刊:Chemical Science
[The Royal Society of Chemistry]
日期:2023-01-01
卷期号:14 (7): 1715-1723
被引量:5
摘要
The integration of oxidation and enantioselective reduction enables a redox deracemization to directly access enantioenriched products from their corresponding racemates. However, the solution of the kinetically microscopic reversibility of substrates used in this oxidation/reduction unidirectional event is a great challenge. To address this issue, we have developed a light-driven strategy to enable an efficient redox deracemization of cyclamines. The method combines a photocatalyst and a chiral phosphoric acid in a toluene/aqueous cyclodextrin emulsion biphasic co-solvent system to drive the cascade out-of-equilibrium. Systemic optimizations achieve a feasible oxidation/reduction cascade sequence, and mechanistic investigations demonstrate a unidirectional process. This single-operation cascade route, which involves initial photocatalyzed oxidation of achiral cyclamines to cyclimines and subsequent chiral phosphoric acid-catalyzed enantioselective reduction of cyclimines to chiral cyclamines, is suitable for constructing optically pure indolines and tetrahydroquinolines.
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