Asymmetric Synthesis of iso-Boc (S)-2-Amino-8-nonenoic Acid in One Through-Process

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• 作者：Jeonghan Park ; Jeffrey C. Moore ; Feng Xu
• 刊名：Organic Process Research & Development
• 出版年：2016
• 出版时间：January 15, 2016
• 年：2016
• 卷：20
• 期：1
• 页码：76-80
• 全文大小：284K
• ISSN：1520-586X

文摘

A practical through-process to prepare iso-Boc (S)-2-amino-8-nonenoic acid has been developed. The short synthesis utilizes a highly enantioselective, enzymatic reductive amination of an α-keto acid substrate, which is prepared via a Grignard addition to diethyl oxalate. Starting from 7-bromohept-1-ene and without isolation of any intermediates, iso-Boc (S)-2-amino-8-nonenoic acid is prepared in 60% overall yield and >99.9% ee.