Highly enantiopure (tert-butyldiphenylsilyloxymethyl)oxiranes from barium carbonate

Article abstract of DOI:10.1080/00397919808004924

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.

Full text of DOI:10.1080/00397919808004924

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Synthetic Communications:
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Highly Enantiopure (tert-
Butyldiphenylsilyloxymethyl)Oxi
from Barium Carbonate
I. VictorEkhato a & Mark Palazzolo a
a Department of Chemical Development , Parke-
Davis Pharmaceutical Research, Division of
Warner-Lambert Company , 2800 Plymouth
Road, Ann Arbor, Michigan, 48105
Published online: 23 Aug 2006.
To cite this article: I. VictorEkhato & Mark Palazzolo (1998) Highly Enantiopure
(tert-Butyldiphenylsilyloxymethyl)Oxiranes from Barium Carbonate, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 28:20, 3727-3741, DOI: 10.1080/00397919808004924
To link to this article: http://dx.doi.org/10.1080/00397919808004924
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