Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (Articolo in rivista)

Type
Label
  • Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (Articolo in rivista) (literal)
Anno
  • 2006-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2006.11.041 (literal)
Alternative label
  • Laura Palombi; Maria Rosaria Acocella; Nicoletta Celenta; Antonio Massa; Rosaria Villano; Arrigo Scettri (2006)
    Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Laura Palombi; Maria Rosaria Acocella; Nicoletta Celenta; Antonio Massa; Rosaria Villano; Arrigo Scettri (literal)
Pagina inizio
  • 3300 (literal)
Pagina fine
  • 3303 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 17 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 23 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica, Universita` degli Studi, Via Ponte don Melillo, I-84084 Fisciano, Salerno, Italy (literal)
Titolo
  • Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system (literal)
Abstract
  • This paper reports the regio-, diastereo- and highly enantioselective vinylogous aldol reaction of 2-trimethylsilyloxyfuran (TMSOF) promoted by the SiCl4/Lewis base catalytic system. Several electron-pair donors proved to be effective as SiCl4 activators versus the TMSOF gamma-selective addition to aldehydes giving rise to different diastereoisomeric ratios, while Denmark's chiral bis-phosphoramide (R,R)-7 gave the highest enantioselectivity for both the anti- and syn-diastereoisomers. Furthermore, by using ambident electrophiles such as alpha,beta-unsaturated aldehydes, the SiCl4/Lewis base-promoted process leads exclusively to the 1,2-addition products. (literal)
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