Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 23, Pages 12049-12064Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402099p
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Funding
- Miur-Rome [PRIN 20099PKPHH_004]
- Fondazione del Monte di Bologna e Ravenna
- COST Action [CM0905]
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An efficient and highly enantioselective Michael addition of nitroalkanes to 3-ylidene oxindoles is described, mediated by thiourea-based bifunctional organocatalysts. The stereochemistry at C-alpha and C-beta centers is perfectly controlled, and the intermediate C-3 enolate is trapped with a second Michael acceptor. The developed one-pot three-component consecutive reactions generate up to four contiguous stereocenters, including the C-3 all-carbon quaternary center, in a perfectly defined configuration. The conversion of the beta-nitro oxindole into the corresponding beta-amino derivative discloses synthetically useful transformations, exploitable to generate pharmaceutically attractive molecular targets.
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