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Synthesis 2010(23): 4068-4074  
DOI: 10.1055/s-0030-1258275
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Amino-5-hydroxycaprolactam Derivatives Mediated by E-Selective Olefination and Asymmetric Oxidation of the Enol Ether

Hong Lia,c, Yingxue Liua, Qijun Liua,c, Wenhui Hua, Guo-Chun Zhou*a,b
a Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, P. R. of China
b College of Biotechnology and Pharmaceutical Engineering and College of Pharmaceutical Sciences, Nanjing University of Technology, Nanjing 210009, P. R. of China
Fax: +86(20)32015351; e-Mail: allspringzhou@yahoo.com;
c Graduate School of Chinese Academy of Sciences, Beijing 100039, P. R. of China
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Publication History

Received 5 August 2010
Publication Date:
30 September 2010 (online)

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Abstract

The asymmetric synthesis of 2-amino-5-hydroxycaprolactam derivatives is essential for exploring the antitumor properties of ester-bearing bengamides. In this study, chiral caprolactam isomers were achieved on the basis of highly E-selective Wittig olefination, asymmetric oxidations of the E-enol ethers, reductive amination of the aldehyde derivatives, cyclization of the 5-hydroxy­lysine analogues or/and deprotection.

Key words

caprolactam - E-selective olefination - asymmetric oxidation - enol ether - reductive amination