Highly Enantiopure (tert-Butyldiphenylsilyloxymethyl)Oxiranes from Barium Carbonate |
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Authors: | I VictorEkhato Mark Palazzolo |
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Institution: | Department of Chemical Development , Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company , 2800 Plymouth Road, Ann Arbor, Michigan, 48105 |
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Abstract: | 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. |
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Keywords: | Basic catalyst Benzoins π‐Excessive heterocycles Isomerization Solvent polarity |
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