Dual catalysis for enantioselective convergent synthesis of enantiopure vicinal amino alcohols

Chen-Xi Ye, Yared Yohannes Melcamu, Heng-Hui Li, Jiang-Tao Cheng, Tian-Tian Zhang, Yuan-Ping Ruan, Xiao Zheng (), Xin Lu () and Pei-Qiang Huang ()
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Chen-Xi Ye: Xiamen University
Yared Yohannes Melcamu: Xiamen University
Heng-Hui Li: Xiamen University
Jiang-Tao Cheng: Xiamen University
Tian-Tian Zhang: Xiamen University
Yuan-Ping Ruan: Xiamen University
Xiao Zheng: Xiamen University
Xin Lu: Xiamen University
Pei-Qiang Huang: Xiamen University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Enantiopure vicinal amino alcohols and derivatives are essential structural motifs in natural products and pharmaceutically active molecules, and serve as main chiral sources in asymmetric synthesis. Currently known asymmetric catalytic protocols for this class of compounds are still rare and often suffer from limited scope of substrates, relatively low regio- or stereoselectivities, thus prompting the development of more effective methodologies. Herein we report a dual catalytic strategy for the convergent enantioselective synthesis of vicinal amino alcohols. The method features a radical-type Zimmerman–Traxler transition state formed from a rare earth metal with a nitrone and an aromatic ketyl radical in the presence of chiral N,N′-dioxide ligands. In addition to high level of enantio- and diastereoselectivities, our synthetic protocol affords advantages of simple operation, mild conditions, high-yielding, and a broad scope of substrates. Furthermore, this protocol has been successfully applied to the concise synthesis of pharmaceutically valuable compounds (e.g., ephedrine and selegiline).

Date: 2018
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DOI: 10.1038/s41467-017-02698-4

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