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

被引：52

作者：

Matsugi, M ^{[1
]}

Fukuda, N ^{[1
]}

Muguruma, Y ^{[1
]}

Yamaguchi, T ^{[1
]}

Minamikawa, J ^{[1
]}

Otsuka, S ^{[1
]}

机构：

[1] Otsuka Pharmaceut Co Ltd, Tokushima Factory 2, Proc Res Dept, Tokushima 7710182, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 14期

关键词：

asymmetric induction; catalysts; oxidation; sulfoxides; titanium acid compounds;

D O I：

10.1016/S0040-4020(01)00152-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective catalytic asymmetric oxidation of prochiral sulfide 1a to (S)-2a has been achieved by the use of chiral titaniummandelic 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 degreesC). Thus a practical synthetic method for the platelet adhesion inhibitor, OPC-29030, was established utilising asymmetric oxidation of 1a. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2739 / 2744

页数：6

共 19 条

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