Stereo- and enantioselective synthesis of acetylenic 2-amino-1,3-diol stereotriads.
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.
Voituriez
Arnaud
A
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.
Pérez-Luna
Alejandro
A
Ferreira
Franck
F
Botuha
Candice
C
Chemla
Fabrice
F
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
D000480:Alkynes; D000588:Amines; D007097:Imines; D015032:Zinc