Tetrahedron

β 3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines

…, X Ginesta, PW Sutton, J Taltavull, F Egeler, P Romea…

文献索引：Farras, Jaume; Ginesta, Xavier; Sutton, Peter W; Taltavull, Joan; Egeler, Frank; Romea, Pedro; Urpi, Felix; Vilarrasa, Jaume Tetrahedron, 2001 , vol. 57, # 36 p. 7665 - 7674

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被引用次数: 40

摘要

N-Nosyl aziridines can be easily prepared from 1, 2-amino alcohols derived from α-amino acids. Nucleophilic ring-opening of N-nosyl aziridines with cyanide ions followed by hydrolysis of the corresponding nitriles lead to N-nosyl β3-amino acids, which can be readily converted into a variety of derivatives bearing adequate functionality for peptide synthesis. The proposed methodology is simple, efficient, and amenable to large-scale preparations.