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.
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|Titolo:||Transformation of Glutamic Acid into (S)-Benzyl 2-(dibenzylamino)- 6-(dimethoxyphosphoryl)-5-oxohexanoate for a Convenient Access to 5-Substituted Prolines.|
|Citazione:||Cini, E., Giorgi, G., Rodriquez, M., & Taddei, M. (2009). Transformation of Glutamic Acid into (S)-Benzyl 2-(dibenzylamino)- 6-(dimethoxyphosphoryl)-5-oxohexanoate for a Convenient Access to 5-Substituted Prolines. SYNLETT(10), 1562-1566.|
|Appare nelle tipologie:||1.1 Articolo in rivista|
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