Alkene Syn Dihydroxylation with Malonoyi Peroxides
Alkene Syn Dihydroxylation with Malonoyi Peroxides
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DOI：
10.1021/ja1066674
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发表时间：
2010-10-20
影响因子：
15
通讯作者：
Tomkinson, Nicholas C. O.
中科院分区：
文献类型：
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作者：
Griffith, James C.;Jones, Kevin M.;Tomkinson, Nicholas C. O.
过氧化环丙基丙二酰（1）是一种有效的烯烃二羟基化试剂，可由市售二元酸一步制备。1与烯烃在1当量水的存在下在40 ° C下反应，然后碱性水解，得到相应的二醇（40-93%）。对于1，2-二取代的烯烃，反应以顺式选择性（3：1至> 50：1）进行。提出了一种与氧标记研究支持的实验结果一致的机制。
Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 degrees C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to > 50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.