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

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

doi:10.2174/157017806777828385

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.

Keywords: BILN-2061, terminal olefin, long chain, optically pure α-amino acid, Synthesis

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Letters in Organic Chemistry

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

Volume: 3 Issue: 6

Author(s): Ge Li, Shu-Hui Chen, Rujian Ma, Suhan Tang, Yifeng Shi, Jingchao Dong, Zhiliu Zhang, Wei Miao and Lanqi Jia

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Keywords: BILN-2061, terminal olefin, long chain, optically pure α-amino acid, Synthesis

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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Li Ge, Chen Shu-Hui, Ma Rujian, Tang Suhan, Shi Yifeng, Dong Jingchao, Zhang Zhiliu, Miao Wei and Jia Lanqi, Efficient Method for the Synthesis of Optically Pure Terminal Olefin Bearing Long Chain α-Amino Acids, Letters in Organic Chemistry 2006; 3 (6) . https://dx.doi.org/10.2174/157017806777828385