| Abstract
| - A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone,using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. Thescope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protectingthe two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivativesunder basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two differentenantiopure products: an α-aryl-α-methoxy-α-trifluoromethyl ethanal and an α-aryl-α-methoxycarboxylicacid. The overall process is eventually an interesting way to convert one natural chiral raw material intotwo functionalized enantiopure building blocks including a trifluoromethyl one.
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