Organic Letters
Organic Letters
5 years ago

Highly Enantioselective Synthesis of syn-β-Hydroxy α-Dibenzylamino Esters via DKR Asymmetric Transfer Hydrogenation and Gram-Scale Preparation of Droxidopa

Highly Enantioselective Synthesis of syn-β-Hydroxy α-Dibenzylamino Esters via DKR Asymmetric Transfer Hydrogenation and Gram-Scale Preparation of Droxidopa
Xiaodong Han, Guodong Sun, Yicao Lin, Lei Chen, Zhongqing Wang, Shun Li, Hailong Wang, Zihong Zhou, Jiebin Zeng, Benquan Hu, Weilin Jian, Yongbo Xu, Zhonghua Luo
A highly efficient preparation of enantiomerically pure syn aryl β-hydroxy α-dibenzylamino esters is reported. The outcome was achieved via dynamic kinetic resolution and asymmetric transfer hydrogenation of aryl α-dibenzylamino β-keto esters. The desired products were obtained in high yields (up to 98%) with excellent diastereoselectivity (>20:1 dr) and enantioselectivity (up to >99% ee). Furthermore, this method was applied for the gram-scale preparation of droxidopa.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01982

DOI: 10.1021/acs.orglett.7b01982

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