Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 22, Pages 6558-6562Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803162
Keywords
asymmetric catalysis; C-C bond cleavage; cobalt; cycloaddition; cyclopropanes
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Funding
- Ministry of Education (Singapore)
- Nanyang Technological University [RG 3/15, RG 114/15, MOE2016-T2-2-043]
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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.
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