jo3001063_si_001.pdf (3.39 MB)
One-Pot in Situ Formation and Reaction of Trimethyl(trichloromethyl)silane: Application to the Synthesis of 2,2,2-Trichloromethylcarbinols
journal contribution
posted on 2012-03-16, 00:00 authored by Kevin E. Henegar, Ricardo Lira2,2,2-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.