Efficient Method for the Synthesis of Optically Pure Terminal Olefin Bearing Long Chain α-Amino Acids

Wei Miao; Lanqi Jia; Zhiliu Zhang; Jingchao Dong; Yifeng Shi; Rujian Ma; Suhan Tang; Shu-Hui Chen; Ge Li

doi:10.2174/157017806777828385

ISSN: 1570-1786
E-ISSN: 1875-6255

Efficient Method for the Synthesis of Optically Pure Terminal Olefin Bearing Long Chain α-Amino Acids
Authors: Wei Miao¹, Lanqi Jia², Zhiliu Zhang³, Jingchao Dong⁴, Yifeng Shi⁵, Rujian Ma⁶, Suhan Tang⁷, Shu-Hui Chen⁸ and Ge Li⁹
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¹ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ² WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ³ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁴ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁵ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁶ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁷ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁸ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China. ⁹ WuXi PharmaTech Co. Ltd.,288 FuTe Zhong Road, No.1 Building, WaiGaoQiao Free Trade Zone,Shanghai 200131, China.
Source: Letters in Organic Chemistry, Volume 3, Issue 6, Jun 2006, p. 489 - 491
DOI: https://doi.org/10.2174/157017806777828385
- Available online: 01 Jun 2006

Abstract

We present herein a general method for the preparation of chiral terminal olefin bearing long chain α- amino acids via the following three-step sequence starting from (S)-N-Boc-2-pyrrolidone-5-carboxylic acid: (1) opening of the γ-lactam ring by an organometallic reagent, (2) keto reduction, and (3) ester hydrolysis.

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2006-06-01

2025-10-13

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Article Type: Research Article

Keyword(s): BILN-2061; long chain; optically pure α-amino acid; Synthesis; terminal olefin

Efficient Method for the Synthesis of Optically Pure Terminal Olefin Bearing Long Chain α-Amino Acids

Abstract

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