L-Glutamic acid was transformed into δ-keto-phosphonate in two steps. This compound was employed in the stereocontrolled synthesis of cis-5-substituted prolines through a Woodward-Horner-Emmons (WHE) reaction with different aldehydes followed by hydrogenolysis/hydrogenation-mediated ring closure. We found also that a one-pot sequential hydroformylation - WHE reaction was possible with cis-5-substituted prolines. In addition to differently functionalised prolines, an indolizidine amino acid with a structure related to constrained peptidomimetics was obtained. © Georg Thieme Verlag Stuttgart.
Transformation of glutamic acid into (S)-benzyl 2-(dibenzylamino)-6- (dimethoxyphosphoryl)-5-oxohexanoate for a convenient access to 5-substituted prolines / Cini, E.; Giorgi, G.; Rodriquez, M.; Taddei, M.. - In: SYNLETT. - ISSN 0936-5214. - 2009:10(2009), pp. 1562-1566. [10.1055/s-0029-1217340]
Transformation of glutamic acid into (S)-benzyl 2-(dibenzylamino)-6- (dimethoxyphosphoryl)-5-oxohexanoate for a convenient access to 5-substituted prolines
Rodriquez M.;
2009
Abstract
L-Glutamic acid was transformed into δ-keto-phosphonate in two steps. This compound was employed in the stereocontrolled synthesis of cis-5-substituted prolines through a Woodward-Horner-Emmons (WHE) reaction with different aldehydes followed by hydrogenolysis/hydrogenation-mediated ring closure. We found also that a one-pot sequential hydroformylation - WHE reaction was possible with cis-5-substituted prolines. In addition to differently functionalised prolines, an indolizidine amino acid with a structure related to constrained peptidomimetics was obtained. © Georg Thieme Verlag Stuttgart.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
