Catalytic asymmetric oxidation of sulfide with titanium–mandelic acid complex: practical synthesis of ( S)-3-[1-(2-methylphenyl)imidazol-2-ylsulfinyl]propan-1-ol, the key intermediate of OPC-29030

An effective catalytic asymmetric oxidation of prochiral sulfide 1a to ( S)- 2a has been achieved by the use of chiral titanium–mandelic acid complex. The enantioselectivity was found to be not influenced by moisture, and moderate to high selectivity (76% ee) was obtained at room temperature (25°C)....

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Bibliographic Details
Published in:Tetrahedron 2001-04, Vol.57 (14), p.2739-2744
Main Authors: Matsugi, Masato, Fukuda, Norio, Muguruma, Yasuaki, Yamaguchi, Taizo, Minamikawa, Jun-ichi, Otsuka, Sei
Format: Article
Language:English
Subjects:
asymmetric induction
catalysts
oxidation
sulfoxides
titanium and compounds
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Summary:An effective catalytic asymmetric oxidation of prochiral sulfide 1a to ( S)- 2a has been achieved by the use of chiral titanium–mandelic acid complex. The enantioselectivity was found to be not influenced by moisture, and moderate to high selectivity (76% ee) was obtained at room temperature (25°C). Thus a practical synthetic method for the platelet adhesion inhibitor, OPC-29030, was established utilising asymmetric oxidation of 1a. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00152-1