215807-86-6Relevant articles and documents
Highly enantiopure (tert-butyldiphenylsilyloxymethyl)oxiranes from barium carbonate
Ekhato, I. Victor,Palazzolo, Mark
, p. 3727 - 3741 (2007/10/03)
The synthesis of (2R)-(tert-butyldiphenylsilyloxymethyl)oxirane and the (2S)-enantiomer from barium carbonate was developed. Methyl glycolate or the hydroxamate analog was prepared and in turn reacted with (S)-(-)-methyl p- tolylsulfoxide or the (R)-enantiomer to make β-keto sulfoxides. From the sulfoxides, we made the diastereoisomeric alcohols in a highly selective sulfoxide group directed hydride reduction, and a Pummerer rearrangement reaction followed by deprotection yielded the enantiomeric diols. (2R)- (tert-Butyldiphenylsilyloxymethyl)oxirane and its (2S)-enantiomer were derived from these diols in an overall yield of 56 % from barium carbonate. This method was developed to provide a convenient access to isotope-labeled analogs of these compounds.