Asymmetric Synthesis of 2 H-Azirine 2-Carboxylate Esters

…, CH Liang, GV Reddy, Y Zhang, T Fang…

文献索引：Davis, Franklin A.; Liu, Hu; Liang, Chang-Hsing; Reddy, G. Venkat; Zhang, Yulian; Fang, Tianan; Titus, Donald D. Journal of Organic Chemistry, 1999 , vol. 64, # 24 p. 8929 - 8935

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被引用次数: 57

摘要

2 H-Azirine 2-carboxylate esters (5), the smallest unsaturated nitrogen heterocycle, are readily prepared in enantiomerically pure form via the base-induced elimination of sulfenic acid (RSOH) from nonracemic N-sulfinylaziridine 2-carboxylate esters (4). Optimum yields were obtained when the aziridine was treated with TMSCl at-95° C followed by LDA, which was attributed to the improved leaving group ability of an silicon-oxonium species. By ...