Stereo- and Enantioselective Synthesis of Acetylenic 2-Amino-1,3-diol Stereotriads

Arnaud Voituriez (1) , Alejandro Pérez-Luna (1) , Franck Ferreira (1) , Candice Botuha (1) , Fabrice Chemla (1)

1 CO - Chimie Organique

The high-yielding and highly efficient stereoselective synthesis of enantiopure anti,anti and syn,anti acetylenic 2-amino-1,3-diol stereotriads from r-alkoxy-tert-butanesulfinylimines bearing a stereocenter r to the imino group is reported. The stereoselectivity of the reaction of these tert-butanesulfinyl (tBS)-imines with allenylzinc (()-1 was found to be controlled only by the configuration of the tBS group. An excellent kinetic resolution of the racemic allenylzinc species was observed, allowing a high stereocontrol no matter what the configuration or the protecting group of the r-alkoxy group.

Domaines: Chimie

Arnaud Voituriez, Alejandro Pérez-Luna, Franck Ferreira, Candice Botuha, Fabrice Chemla. Stereo- and Enantioselective Synthesis of Acetylenic 2-Amino-1,3-diol Stereotriads. Organic Letters, 2009, 11 (4), pp.931-934. ⟨10.1021/ol802912f⟩. ⟨hal-03883244⟩