Cobalt-catalyzed intramolecular reactions between a vinylcyclopropane and an alkyne : switchable [5+2] cycloaddition and homo-ene pathways

• Main Authors: Wu, Chunlin, Yoshikai, Naohiko
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2019
• Subjects: Asymmetric Catalysis; C-C Bond Cleavage; DRNTU::Science::Chemistry
• Online Access: https://hdl.handle.net/10356/105752; http://hdl.handle.net/10220/48731
• Institution: Nanyang Technological University

Cobalt–diphosphine catalysts have been found to promote intramolecular reactions between a vinylcyclopropane and an alkyne to selectively afford either the [5+2] cycloaddition 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 dimethylacetamide. Furthermore, a highly enantioselective variant of the homo‐ene reaction afforded chiral tetrahydrofuran, pyrrolidine, and cyclopentane derivatives bearing 1,3‐diene and alkylidene substituents.