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Copper(I)‐Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring‐Opening C−C Bond Formations
Author(s) -
Zhang Hang,
Wu Guojiao,
Yi Heng,
Sun Tong,
Wang Bo,
Zhang Yan,
Dong Guangbin,
Wang Jianbo
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.201612138
Subject(s) - chemoselectivity , chemistry , diazo , ring (chemistry) , catalysis , copper , coupling (piping) , medicinal chemistry , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy
Reported herein is an exceptional chemoselective ring‐opening/C(sp 3 )−C(sp 3 ) bond formation in the copper(I)‐catalyzed reaction of cyclopropanols with diazo esters. The conventional O−H insertion product is essentially suppressed by judicious choice of reaction conditions. DFT calculations provide insights into the reaction mechanism and the rationale for this unusual chemoselectivity.