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  • Trichloromethyltrimethylsilane, Sodium Formate,and Dimethylformamide: A Mild, Efficient, andGeneral Method for the Preparation ofTrimethylsilyl-Protected2,2,2-Trichloromethylcarbinols from Aldehydesand Ketones
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  • New conditions for the preparation of trimethylsilyl-protected2,2,2-trichloromethylcarbinols 2 from aldehydes and ketonesare reported. Compounds 2, which are important intermediates in organic synthesis, were obtained in excellent yieldsby use of a combination of trichloromethyltrimethylsilane(TMSCCl3), and a catalytic amount of sodium formate(HCOONa) in dimethylformamide (DMF). Substrates bearing highly sensitive protecting groups have been successfullysubjected to our conditions. We also describe a one-potprocedure that gives direct access to 2,2,2-trichloromethylcarbinols 3. This methodology avoids the use of strong basesusually required for the synthesis of 3 (Wyvratt et al. J. Org.Chem. 1987, 52, 944; Aggarwal and Mereu, J. Org. Chem.2000, 65, 7211).
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