Premium
Synthesis of Substituted Pyrroles via Copper‐Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides
Author(s) -
Lu Kui,
Ding Fang,
Qin Long,
Jia Xiaoliang,
Xu Chuanming,
Zhao Xia,
Yao Qingwei,
Yu Peng
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600761
Subject(s) - isocyanide , annulation , moiety , chemistry , aryl , catalysis , copper , sulfonyl , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
A new method for the synthesis of di‐ and trisubstituted pyrroles via copper‐catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron‐withdrawing group in the α‐carbon of the isocyanide, was found to migrate to the γ‐carbon of the starting allenoate in the final product for the first time.