Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates (Articolo in rivista)

Type
Label
  • Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/adsc.201100572 (literal)
Alternative label
  • Andrea Sartori, Luca Dell'Amico, Claudio Curti, Lucia Battistini, Giorgio Pelosi, Gloria Rassu, Giovanni Casiraghi and Franca Zanardi (2011)
    Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates
    in Advanced synthesis & catalysis (Internet); Wiley-Blackwell, Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Andrea Sartori, Luca Dell'Amico, Claudio Curti, Lucia Battistini, Giorgio Pelosi, Gloria Rassu, Giovanni Casiraghi and Franca Zanardi (literal)
Pagina inizio
  • 3278 (literal)
Pagina fine
  • 3284 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1615-4169 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 353 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 7 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 18 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Università degli Studi di Parma Consiglio Nazionale delle Ricerche (literal)
Titolo
  • Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates (literal)
Abstract
  • A catalyst-free, environmentally benign three-component vinylogous Mukaiyama-Mannich reaction of pyrrole-based silyl dienolates is presented, which works effectively in both aqueous and solvent-free environments. Both lipophilic and hydrophilic aldehyde candidates are suitable substrates, allowing access to a rich repertoire of unsaturated vicinal aminolactam structures with virtually complete g-site selectivity and moderate to good anti-diastereoselectivity. The utility of this technology is highlighted by protecting group-free synthesis of densely hydroxylated, sugar-related lactam frameworks. The role of water as an indispensable H-bonding reaction propeller is demonstrated. (literal)
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