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Silver‐Catalyzed Three‐Component 1,1‐Aminoacylation of Homopropargylamines: α‐Additions for Both Terminal Alkynes and Isocyanides
Author(s) -
Tong Shuo,
Piemontesi Cyril,
Wang Qian,
Wang MeiXiang,
Zhu Jieping
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704727
Subject(s) - aminoacylation , terminal (telecommunication) , catalysis , component (thermodynamics) , chemistry , combinatorial chemistry , computer science , organic chemistry , physics , transfer rna , biochemistry , telecommunications , rna , gene , thermodynamics
Abstract The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three‐component reaction with isocyanides and carboxylic acids to afford functionalized N‐acyl proline amides. High diastereoselectivity was observed in the synthesis of 4‐alkoxy and 4,5‐disubstituted proline derivatives. This work represents the first examples of a three‐component cyclizative 1,1‐aminoacylation of terminal alkynes.