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Asymmetric synthesis of α-amino acids by alkylation of a glycine amide derivative bearing chiral 2,5-disubstituted pyrrolidine as an amine component

✍ Scribed by Satoru Ikegami; Takashi Hayama; Tsutomu Katsuki; Masar-u Yamaguchi

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
260 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Highly diastereoselective alkylation (296% de) of a-lithiated N-[N'-bis(methylthio)---methyleneglycyl~-~-2,5-bis~methoxymethoxymethyl~pyrrolidine and subsequent hydrolysis gave a-amino acids of high optical purity.

An unusual amino acid (2S,9_S)-2-amino-8-oxo-9,10epoxydecanoic acid was synthesized in its N-protected form as an application of the method.

📜 SIMILAR VOLUMES

A highly effective asymmetric synthesis
A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine
✍ Masayuki Enomoto; Yoshio Ito; Tsutomu Katsuki; Masaru Yamaguchi 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 169 KB

Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine proceeded with high stereoselectivity (196% de) and subsequent transformations of the alkylated products gave synthetically useful o-benzyloxy acids or cr-hydroxy acids of high enantiomeric purity. a-Hydroxy a