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Asymmetric synthesis of α-amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-butyl-N-tosyloxycarbamate

✍ Scribed by Nan Zheng; Joseph D. Armstrong III; J.Christopher McWilliams; R.P. Volante

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
218 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a ( + )NHBOC synthon in highly diastereoselective reactions with chiral cis-aminoindanol derived amide cuprates is described. The diastereoselectivities of these reactions ranged from 96% to greater than 99%. The subsequent transformation of these adducts to a-amino acids is also described.

📜 SIMILAR VOLUMES

Asymmetric synthesis of α-amino acids by
Asymmetric synthesis of α-amino acids by alkylation of a glycine amide derivative bearing chiral 2,5-disubstituted pyrrolidine as an amine component
✍ Satoru Ikegami; Takashi Hayama; Tsutomu Katsuki; Masar-u Yamaguchi 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 260 KB

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