One-Pot Synthesis of Trichloromethyl Carbinols from Primary Alcohols

Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess–Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.