Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines

Mingxu Li; Jian Zhang; Yashi Zou; Fengfan Zhou; Zhenfeng Zhang; Wanbin Zhang

doi:10.1039/d1sc04288b

Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines

Chem Sci. 2021 Oct 28;12(45):15061-15066. doi: 10.1039/d1sc04288b. eCollection 2021 Nov 24.

Authors

Mingxu Li¹, Jian Zhang¹, Yashi Zou¹, Fengfan Zhou¹, Zhenfeng Zhang¹, Wanbin Zhang^{1

2}

Affiliations

¹ Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China zhenfeng@sjtu.edu.cn.
² 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.