Journal
ACS CATALYSIS
Volume 9, Issue 6, Pages 5638-5644Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00655
Keywords
cobalt catalysis; asymmetric catalysis; cyclopropanes; desymmetrization; homoenolate
Categories
Funding
- Ministry of Education (Singapore) [MOE2016-T2-2-043]
- Nanyang Technological University
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We report herein cobalt-catalyzed enantioselective and chemodivergent reactions between a cyclopropanol and an oxabicyclic alkene via a cobalt homoenolate, which afford either an alkylative ring-opening product or a hydroalkylation product, with the counterion of the cobalt catalyst being a major chemoselectivity-controlling factor. A catalyst generated from cobalt(II) chloride and a chiral diphosphine promotes alkylative ring opening to afford 1,2-dihydronaphthalen-1-ol derivatives in good yields with high enantioselectivity. By contrast, a catalyst generated from cobalt(II) acetate and the same diphosphine ligand, with the assistance of methanol, selectively affords hydroalkylation products with retention of the bicyclic structure at a comparable level of enantioselectivity.
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