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 …

…, N Fukuda, Y Muguruma, T Yamaguchi, J Minamikawa…

Index: Matsugi; Fukuda; Muguruma; Yamaguchi; Minamikawa; Otsuka Tetrahedron, 2001 , vol. 57, # 14 p. 2739 - 2744

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Citation Number: 48

Abstract

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.