An efficient enantioselective synthesis of ()-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination.

J Asian Nat Prod Res

Department of Medicinal Chemistry, Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation & State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Bei

Published: January 2020


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Article Abstract

We present the synthesis of enantiomerically pure ()-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di--chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine derivative catalyst. The application of the organocatalyst of D-3-(1-Naphthyl)-alanine is the key step in the synthesis and ensures the product is obtained with high levels of stereocontrol.

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http://dx.doi.org/10.1080/10286020.2019.1634058DOI Listing

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