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Copper(I)‐Catalyzed One‐Pot Synthesis of Highly Functionalized Pyrrolidines from Sulfonyl Azides, Alkynes, and Dimethyl 2‐(Phenylamino)maleate
Author(s) -
Ramanathan Devenderan,
Pitchumani Kasi
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403285
Subject(s) - ketenimine , chemistry , intramolecular force , cycloaddition , sulfonyl , nucleophilic addition , moiety , alkyne , azide , nucleophile , divergent synthesis , combinatorial chemistry , medicinal chemistry , cascade reaction , catalysis , organic chemistry , alkyl
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 cyclization followed by [1,3]‐H shift. The important advantage of this methodology, which allows selective intramolecular nucleophilic attack of the generated ketenimine carbanion on an ester moiety for the first time, is that the starting materials can be easily prepared.