Copper(I)‐Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring‐Opening C−C Bond Formations | Zendy

Zhang Hang | Zendy; Wu Guojiao | Zendy; Yi Heng | Zendy; Sun Tong | Zendy; Wang Bo | Zendy; Zhang Yan | Zendy; Dong Guangbin | Zendy; Wang Jianbo | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201612138

Subject(s) - chemoselectivity , chemistry , diazo , catalysis , ring (chemistry) , copper , medicinal chemistry , coupling (piping) , 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.

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