Transition Metal Catalyzed Asymmetric Oxidation of Sulfides
Transition Metal Catalyzed Asymmetric Oxidation of Sulfides
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过渡金属催化硫化物的不对称氧化
DOI：
10.1002/chin.200905259
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发表时间：
2008
期刊：
影响因子：
--
通讯作者：
E. P. Talsi
中科院分区：
文献类型：
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作者：
K. Bryliakov;E. P. Talsi
在过去的二十年里，手性亚硫醚的应用越来越广泛，这反映了人们对不对称合成中的方便助剂以及具有手性亚硫基的产品的兴趣与日俱增。1984年，Kagan和Modena的研究小组发现，钛(IV)异丙醇盐-酒石酸二乙酯体系(也称为“改良Katsuki-Sharpless试剂”)能够被烷基过氧化氢不对称氧化前手性硫化物。后来，酒石酸钛体系的催化版本被开发出来(某些硫化物的产率高达90%，ee值高达90%)，这些体系仍然是不对称亚硫化反应中应用最广泛的体系。然而，此类体系的低循环次数(5-20)、复杂性和昂贵促使人们寻找其他基于过渡金属的催化体系。本文综述了80年代初至今过渡金属催化不对称硫化物氧化反应的研究进展。
In the past two decades, chiral sulfoxides have been finding increasing use, reflecting growing interest both in convenient auxiliaries in asymmetric synthesis and products with biological properties containing a chiral sulfinyl group. In 1984, groups of Kagan and Modena discovered that titanium(IV) isopropoxide - diethyltartrate based systems (also known as “modified Katsuki-Sharpless reagents”) are capable of asymmetric oxidizing of prochiral sulfides by alkylhydroperoxides. Later, catalytic versions of the titanium tartrate systems were developed (with up to 90 % yield and 90 % ee for certain sulfides) that remain the most applied systems for asymmetric sulfoxidations. However, the low turnover numbers (5-20), complexity and expensiveness of such systems stimulated the search for other transition metal based catalytic systems. This review will cover the progress in transition metal catalyzed asymmetric sulfides oxidations achieved since the discoveries of early 1980s to the present days.