Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, USA.
J Org Chem. 2013 Sep 6;78(17):8865-71. doi: 10.1021/jo401267j. Epub 2013 Aug 27.
N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaziridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.
N-酰基氮丙啶是手性胺衍生物合成的重要起始原料。传统的生成这些活化氮丙啶的方法存在显著的缺陷。本文描述了通过 N-对甲苯磺酰氮丙啶的脱保护作用和 N-羟基琥珀酰亚胺衍生物的再保护作用来进行 N-酰基氮丙啶的克级规模合成。单取代和双取代氮丙啶的反应效果良好，立体化学纯度完全保留。始终保持中等收率与 N-对甲苯磺酰氮丙啶的脱保护步骤有关，而用 N-羟基琥珀酰亚胺衍生物进行酰化反应则非常高效。
