L-Glutamic acid was transformed into β-keto-phosphonate in two steps.  This compd. 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 addn. to differently functionalized prolines, an indolizidine amino acid with a structure related to constrained peptidomimetics was obtained.

Transformation of Glutamic Acid into (S)-Benzyl 2-(dibenzylamino)-6-(dimethoxyphosphoryl)-5-oxohexanoate for a Convenient Access to 5-Substituted Prolines

RODRIQUEZ, Manuela;
2009

Abstract

L-Glutamic acid was transformed into β-keto-phosphonate in two steps.  This compd. 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 addn. to differently functionalized prolines, an indolizidine amino acid with a structure related to constrained peptidomimetics was obtained.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/2260721
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