Stereoselective synthesis and characterization of new enantiomerically pure phosphoric acids
Articolo
Data di Pubblicazione:
2010
Citazione:
Stereoselective synthesis and characterization of new enantiomerically pure phosphoric acids / C. Biaggi, M. Benaglia, R. Annunziata, S. Rossi,. - In: CHIRALITY. - ISSN 0899-0042. - 22:3(2010), pp. 369-378.
Abstract:
Starting from (R)-6,6′-dimethyldiphenyl-2,2′-dicarboxylic acid, a novel class of enantiomerically pure cyclic dialkyl phosphates was synthesized and properly characterized. The absolute configuration was determined by 2D NOESY experiments. The catalytic behavior of the new chiral Bronsted acids was investigated in the stereoselective addition of a silyl keteneacetal to aldimines. The Mannich-type reaction was promoted in up to 94% yields and enantioselectivities up to 55%. On the basis of preliminary molecular mechanic calculations, a model of stereoselection was also proposed to explain the sense of the enantioselectivity observed in the reaction.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Bronsted acids; Enantioselectivity; Organocatalysis; Phosphoric acids
Elenco autori:
C. Biaggi, M. Benaglia, R. Annunziata, S. Rossi,
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