358720-84-0Relevant academic research and scientific papers
One-pot in situ formation and reaction of trimethyl(trichloromethyl)silane: Application to the synthesis of 2,2,2-trichloromethylcarbinols
Henegar, Kevin E.,Lira, Ricardo
experimental part, p. 2999 - 3004 (2012/05/04)
2,2,2-Trichloromethylcarbinols are 1 are valuable synthetic intermediates with a multitude of uses. A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols 1 was developed that employs the in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS. This procedure was applied to diastereoselective trichloromethyl additions to 2-substituted 4-piperidinones and to reactions with a variety of structurally diverse aldehydes and ketones.
Trichloromethyltrimethylsilane, sodium formate, and dimethylformamide: A mild, efficient, and general method for the preparation of trimethylsilyl- protected 2,2,2-trichloromethylcarbinols from aldehydes and ketones
Kister, Jeremy,Mioskowski, Charles
, p. 3925 - 3928 (2008/02/02)
(Chemical Equation Presented) New conditions for the preparation of trimethylsilyl-protected 2,2,2-trichloromethylcarbinols 2 from aldehydes and ketones are reported. Compounds 2, which are important intermediates in organic synthesis, were obtained in excellent yields by use of a combination of trichloromethyltrimethylsilane (TMSCCI3), and a catalytic amount of sodium formate (HCOONa) in dimethylformamide (DMF). Substrates bearing highly sensitive protecting groups have been successfully subjected to our conditions. We also describe a one-pot procedure that gives direct access to 2,2,2-trichloromethylcarbinols 3. This methodology avoids the use of strong bases usually required for the synthesis of 3 (Wyvratt et al. J. Org. Chem. 1987, 52, 944; Aggarwal and Mereu, J. Org. Chem. 2000, 65, 7211).
