Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines†

Received: 12 Mar 2020, Revised: 14 Mar 2020, Accepted: 10 June 2020, Available online: 18 June 2020, Version of Record: 18 June 2020

Mingxu Li,a Jian Zhang,a Yashi Zou,a Fengfan Zhou,a Zhenfeng Zhang *a and Wanbin Zhang ab

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* Corresponding authors
a Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
E-mail: zhenfeng@sjtu.edu.cn
b Frontier Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China

Abstract


Asymmetric hydrogenation of unsaturated morpholines has been developed by using a bisphosphine-rhodium catalyst bearing a large bite angle. With this approach, a variety of 2-substituted chiral morpholines could be obtained in quantitative yields and with excellent enantioselectivities (up to 99% ee). The hydrogenated products could be transformed into key intermediates for bioactive compounds.
Graphical abstract: Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines



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