Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination

doi:10.1007/s40242-015-4412-z

高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (2): 203-207.doi: 10.1007/s40242-015-4412-z

Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination

ZHANG Xiaohua, YE Wenjing, WANG Kuanglei, TIAN Yongshou, XIAO Xiao

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China

收稿日期:2014-10-29 修回日期:2014-12-10 出版日期:2015-04-01 发布日期:2015-01-19
通讯作者: TIAN Yongshou, XIAO Xiao E-mail:yongshoutian988@163.com;xxiao1207@iccas.ac.cn
基金资助:
Supported by the Natural Science Foundation of China(No.21402127), Foundation of Liaoning Province Education Department(No.L2013381), PhD Research Startup Foundation of Liaoning Province(No.20131110), and Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University.

Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination

ZHANG Xiaohua, YE Wenjing, WANG Kuanglei, TIAN Yongshou, XIAO Xiao

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China

Received:2014-10-29 Revised:2014-12-10 Online:2015-04-01 Published:2015-01-19
Contact: TIAN Yongshou, XIAO Xiao E-mail:yongshoutian988@163.com;xxiao1207@iccas.ac.cn
Supported by:
Supported by the Natural Science Foundation of China(No.21402127), Foundation of Liaoning Province Education Department(No.L2013381), PhD Research Startup Foundation of Liaoning Province(No.20131110), and Career Development Support Plan for Young and Middle-aged Teachers in Shenyang Pharmaceutical University.

摘要/Abstract

摘要：

An efficient phase-transfer-catalyzed directed reductive amination of α-keto esters was described using simple substituted benzyl amines as nitrogen source and K₂CO₃as base at room temperature, giving a series of aliphatic α-amino acid derivatives in moderate to high yields(up to 99%). Preliminary study on this asymmetric process showed that cinchona-derived phase transfer catalyst was effective, affording the corresponding product in 13% e.e. and 40% yield.

关键词: Directed reductive amination, α-Amino acid, Phase transfer catalyst

Abstract:

Key words: Directed reductive amination, α-Amino acid, Phase transfer catalyst

ZHANG Xiaohua, YE Wenjing, WANG Kuanglei, TIAN Yongshou, XIAO Xiao. Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination[J]. 高等学校化学研究, 2015, 31(2): 203-207.

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Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination

Efficient Synthesis of α-Amino Acid Derivatives via Phase-transfer-catalyzed Directed Reductive Amination

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