Synthesis of fluorinated pseudopeptides: metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2011

Synthesis of fluorinated pseudopeptides: metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines.

Résumé

The addition reaction of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines was studied. Depending of the nature of the organometallic species (Grignard reagents or zincate complexes), we were able to control the configuration of the newly created stereogenic centers in high yields with good to high diastereomeric ratios. The chiral β-fluoro allylamines are key synthons toward the synthesis of fluorinated pseudopeptides bearing a fluoroolefin moiety as a peptide bond mimic.

Domaines

Chimie organique
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Dates et versions

hal-00991652 , version 1 (15-05-2014)

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Camille Pierry, Dominique Cahard, Samuel Couve-Bonnaire, Xavier Pannecoucke. Synthesis of fluorinated pseudopeptides: metal mediated reversal of stereochemistry in diastereoselective addition of organometallic reagents to N-(tert-butanesulfinyl)-α-fluoroenimines.. Organic & Biomolecular Chemistry, 2011, 9 (7), pp.2378-2386. ⟨10.1039/c0ob00773k⟩. ⟨hal-00991652⟩
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