Journal
ORGANIC LETTERS
Volume 11, Issue 4, Pages 931-934Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802912f
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- CNRS
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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.
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