✦ LIBER ✦

Asymmetric synthesis of α-amino acids by alkylation of N-[N-bis-(methylthio)methyleneglycyl]-2,5-bis(methoxymethoxymethyl)pyrrolidine and enantioselective synthesis of protected (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid

✍ Scribed by Satoru Ikegami; Harumi Uchiyama; Takashi Hayama; Tsutomu Katsuki; Masaru Yamaguchi

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 723 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86040-3

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✦ Synopsis

Highly diastereoselective alkylation (196% de) of a-lithiated E-INbis(methylthio)methyleneglycyll-trans-2,5-b~s~methoxymethoxymethyl~pyrrol~~lne and subsequent hydrolysis gave various a-amino acids of high optical purity. An unusual amino acid (2S,9S)-2-amrno-8-oxo-9,lO-epoxydecanolc acid was also synthesized enantioseTecirvely in its N-protected form by using

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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