Copper(I)-Catalyzed One-Pot Synthesis of Highly Functionalized Pyrrolidines from Sulfonyl Azides, Alkynes, and Dimethyl 2-(Phenylamino)maleate
作者:Devenderan Ramanathan、Kasi Pitchumani
DOI:10.1002/ejoc.201403285
日期:2015.1
An efficient one-pot synthesis of highly functionalized pyrrolidines by using sulfonyl azides, alkynes, and dimethyl 2-(phenylamino)maleate catalyzed by copper(I)–Y zeolite under mild reaction conditions was investigated. This cascade process involves an azide–alkyne [3+2] cycloaddition/ring rearrangement/ketenimine formation/intermolecular nucleophilic addition cascade and consequent intramolecular
研究了在温和的反应条件下,在铜 (I)-Y 沸石的催化下,使用磺酰叠氮化物、炔烃和 2-(苯基氨基)马来酸二甲酯高效一锅法合成高度官能化的吡咯烷。该级联过程涉及叠氮化物-炔[3+2] 环加成/环重排/烯酮亚胺形成/分子间亲核加成级联和随后的分子内环化,然后是[1,3]-H 位移。这种方法的重要优点是首次允许生成的烯酮亚胺碳负离子对酯部分进行选择性分子内亲核攻击,其重要优势在于可以轻松制备起始材料。