Copper(I)-Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring-Opening C-C Bond Formations

被引：64
|
作者：
Zhang, Hang [1 ,2 ]
Wu, Guojiao [1 ,2 ]
Yi, Heng [1 ,2 ]
Sun, Tong [1 ,2 ]
Wang, Bo [1 ,2 ]
Zhang, Yan [1 ,2 ]
Dong, Guangbin [3 ]
Wang, Jianbo [1 ,2 ]
机构：
[1] Peking Univ, Minist Educ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China
[2] Peking Univ, Minist Educ, Coll Chem, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[3] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 14期
关键词：
carbenes; C C coupling reactions; copper; diazo compounds; small ring compounds; O-H INSERTION; ALPHA-DIAZOCARBONYL COMPOUNDS; CATALYZED 3+2 CYCLOADDITION; DIAZO-COMPOUNDS; MOLECULAR CALCULATIONS; CARBENE INSERTION; GOLD CATALYSIS; FUNCTIONALIZATION; CHEMISTRY; DENSITY;
D O I：
10.1002/anie.201612138
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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.
引用
收藏
页码：3945 / 3950
页数：6
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