Direct and Enantioselective Vinylogous Michael Addition of alfa-Ethylidene Pyrazolinones to Nitroolefins Catalyzed by Dual Cinchona Alkaloid Thioureas (Articolo in rivista)

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  • Direct and Enantioselective Vinylogous Michael Addition of alfa-Ethylidene Pyrazolinones to Nitroolefins Catalyzed by Dual Cinchona Alkaloid Thioureas (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Alternative label
  • Rassu, G.; Zambrano, V.; Pinna, L.; Curti, C.; Battistini, L.; Sartori, A.; Pelosi, G.; Zanardi, F.; Casiraghi, G. (2014)
    Direct and Enantioselective Vinylogous Michael Addition of alfa-Ethylidene Pyrazolinones to Nitroolefins Catalyzed by Dual Cinchona Alkaloid Thioureas
    in Advanced synthesis & catalysis (Print); Wiley-VCH - Weinheim, Wheinheim (Germania)
    (literal)
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  • Rassu, G.; Zambrano, V.; Pinna, L.; Curti, C.; Battistini, L.; Sartori, A.; Pelosi, G.; Zanardi, F.; Casiraghi, G. (literal)
Pagina inizio
  • 2330 (literal)
Pagina fine
  • 2336 (literal)
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  • 356 (literal)
Rivista
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  • 7 (literal)
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  • Consiglio Nazionale delle Ricerche - Istituto di Chimica Biomolecolare Università degli Studi di Parma - Dipartimento di Farmacia (literal)
Titolo
  • Direct and Enantioselective Vinylogous Michael Addition of alfa-Ethylidene Pyrazolinones to Nitroolefins Catalyzed by Dual Cinchona Alkaloid Thioureas (literal)
Abstract
  • While several protocols exist for the asymmetric functionalization of pyrazolinones at the alfa-position relying on nucleophilic addition or annulation procedures, use of alfa-ethylidene electron-rich analogues in asymmetric vinylogous coupling to carbon electrophiles is substantially an uncharted domain. We now report, for the first time, that ethylidenepyrazolinones carrying an enolizable carbon at the gamma-position efficiently participate in direct and asymmetric, catalytic vinylogous Michael-type addition to nitroolefins providing the expected adducts in high yields, with complete gamma-site selectivity and with an extraordinary level of geometrical and enantioselectivity. Either R- or S- configured adducts were equally accessed by employing a quasi-enantiomeric quinine- or quinidine-based thiourea catalyst pair. (literal)
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