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Title: Transformation of Glutamic Acid into (S)-Benzyl 2-(dibenzylamino)- 6-(dimethoxyphosphoryl)-5-oxohexanoate for a Convenient Access to 5-Substituted Prolines.
Authors: Cini, Elena 
Giorgi, Gianluca 
Rodriquez, M
Taddei, Maurizio 
Issue Date: 2009
Project: None 
Journal: SYNLETT
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.
ISSN: 0936-5214
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