Cobalt-Catalyzed Intramolecular Reactions between a Vinylcyclopropane and an Alkyne: Switchable [5+2] Cycloaddition and Homo-Ene Pathways

被引：30
|
作者：
Wu, Chunlin [1 ]
Yoshikai, Naohiko [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 22期
关键词：
asymmetric catalysis; C-C bond cleavage; cobalt; cycloaddition; cyclopropanes; COUPLING REACTIONS; METAL; SELECTIVITY; MECHANISM; ORIGINS; ALLENES; CYCLOISOMERIZATION; COMPLEXES; IMINE; IRON;
D O I：
10.1002/anie.201803162
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cobalt-diphosphine catalysts have been found to promote intramolecular reactions between a vinylcyclopropane and an alkyne to selectively afford either the [5+2] cyclo-addition product or the homo-ene reaction product under solvent control. The former product is exclusively formed in noncoordinating 1,2-dichloroethane, whereas the latter is dominant in coordinating solvents, such as acetonitrile and dimethylucetamide. Furthermore, a highly enantioselective variant of the homo-ene reaction afforded chiral tetrahydrofuran, pyrrolidine, and cyclopent ne derivatives bearing 1,3 dime and alkylidene substituents.
引用
收藏
页码：6558 / 6562
页数：5
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