Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 14, Pages 7158-7171Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01022
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- University of Bologna
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The gamma-functionalization of oxindoles bearing nonsymmetric 3-alkylidene groups via vinylogous Michael-type addition to nitroolefins was realized. The suppression of the interconversion between the E and Z isomers of the starting oxindoles allowed a site-specific diastereoselective and enantioselective transformation. Specific experiments allowed us to establish the rate-determining step of the reaction and to advance a robust hypothesis for the exclusive formation of an s-cis enolate as the only reactive intermediate.
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