title: Stereo- and enantioselective synthesis of acetylenic 2-amino-1,3-diol stereotriads.
abstract: The high-yielding and highly efficient stereoselective synthesis of enantiopure anti,anti and syn,anti acetylenic 2-amino-1,3-diol stereotriads from alpha-alkoxy-tert-butanesulfinylimines bearing a stereocenter alpha 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 alpha-alkoxy group.
authors.affiliation: UPMC Univ Paris 06, UMR7611, Laboratoire de Chimie Organique, Institut de Chimie Moléculaire (FR2769), case 183, 4 place Jussieu, F-75252 Paris Cedex 05, France.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Voituriez
authors.forename: Alejandro
authors.initials: A
authors.lastname: Pérez-Luna
authors.forename: Franck
authors.initials: F
authors.lastname: Ferreira
authors.forename: Candice
authors.initials: C
authors.lastname: Botuha
authors.forename: Fabrice
authors.initials: F
authors.lastname: Chemla
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D007097:Imines; D015032:Zinc