Stereochemical aspects of the asymmetric synthesis of chiral alpha,beta-dihydroxy phosphonates. Synthesis of alpha,beta-dihydroxy phosphonic acids (Articolo in rivista)

Type
Label
  • Stereochemical aspects of the asymmetric synthesis of chiral alpha,beta-dihydroxy phosphonates. Synthesis of alpha,beta-dihydroxy phosphonic acids (Articolo in rivista) (literal)
Anno
  • 1996-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0957-4166(96)00456-9 (literal)
Alternative label
  • Bongini A.; Camerini R.; Panunzio M.; Bandini E.; Martelli G.; Spunta G. (1996)
    Stereochemical aspects of the asymmetric synthesis of chiral alpha,beta-dihydroxy phosphonates. Synthesis of alpha,beta-dihydroxy phosphonic acids
    in Tetrahedron: asymmetry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Bongini A.; Camerini R.; Panunzio M.; Bandini E.; Martelli G.; Spunta G. (literal)
Pagina inizio
  • 3485 (literal)
Pagina fine
  • 3504 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/S0957416696004569 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 7 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 12 (literal)
Note
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipto. di Chim. G. Ciamician U., C.S.F.M.-C.N.R., Via Selmi, 2, 40126 Bologna; I.Co.C.E.A.-C.N.R., Via Gobetti, 101-40129 Bologna (literal)
Titolo
  • Stereochemical aspects of the asymmetric synthesis of chiral alpha,beta-dihydroxy phosphonates. Synthesis of alpha,beta-dihydroxy phosphonic acids (literal)
Abstract
  • Stereocontrol in the asymmetric phosphonylation of aldehydes via organophosphorous esters has been obtained starting from chiral aldehydes. The nature of the O-protecting group is crucial to obtain, in terms of diastereoselectivity and chemical yields, the best results. An ab initio molecular orbital study on 2-silyloxy propanal and MM2 studies on 2-alkoxy propanal show the existence of stable cyclic and acyclic conformers, which are presumably responsible for the high syn diastereoselectivity observed in the addition of non-metal carrying phosphites. (literal)
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