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Substrate specificity of the kinetic resolution of sulfides by enantioselective sulfoxide formation

✍ Scribed by Michael L Phillips; Jill A Panetta

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 373 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00205-x

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✦ Synopsis

The kinetic resolution of tazofelone (1) has been reported. The resolution of this sulfide was accomplished via enantioselective sulfoxide formation with tert-Bu hydroperoxide in the presence of a chiral tartrate/titanium complex. The resolution was performed on analogues of compound 1 in order to explore the substrate specificity of the kinetic resolution. These experiments have shown that the success of the enantioselective oxidation of this sulfide by tert-Bu hydroperoxide is greatly influenced by the nature of the neighboring amide functionality.

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