Your browser doesn't support javascript.
loading
P-chiral, monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis.
Colby, Elizabeth A; Jamison, Timothy F.
Afiliação
  • Colby EA; Massachusetts Institute of Technology, Department of Chemistry, Cambridge, Massachusetts 02139, USA.
J Org Chem ; 68(1): 156-66, 2003 Jan 10.
Article em En | MEDLINE | ID: mdl-12515474
Eight P-chiral monodentate ferrocenyl phosphines (1a-h) were prepared in high enantiomeric excess (>95% ee in most cases) by way of an ephedrine-based oxazaphospholidine borane complex. Primary alkyl, secondary alkyl, and substituted aromatic substituents were successfully introduced at the phosphorus center, along with ferrocenyl and phenyl groups, generating phosphines of the general structure FcP(Ph)(R) (Fc = ferrocenyl, R = aryl, alkyl). The synthetic route employed provides facile access to a previously undeveloped class of chiral monophosphines. These compounds were evaluated as ligands in asymmetric catalytic reductive coupling of alkynes and aldehydes and were found to provide the desired chiral allylic alcohols with good regioselectivity and ee in many cases and with complete (E)-selectivity (>98:2) in all cases.
Assuntos
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fosfinas / Boranos / Compostos Ferrosos Idioma: En Revista: J Org Chem Ano de publicação: 2003 Tipo de documento: Article País de afiliação: Estados Unidos
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fosfinas / Boranos / Compostos Ferrosos Idioma: En Revista: J Org Chem Ano de publicação: 2003 Tipo de documento: Article País de afiliação: Estados Unidos