Wurz Ryan P, Charette André B
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Québec, Canada H3C 3J7.
Org Lett. 2002 Dec 12;4(25):4531-3. doi: 10.1021/ol0270879.
[reaction: see text] A cyclopropanation reaction involving ethyl diazoacetate and olefins proceeds with surprisingly high efficiency in aqueous media using Rh(II) carboxylates. Nishiyama's Ru(II) Py-box and Katsuki's Co(II) Salen complexes that allow for highly enantioselective cyclopropanations in organic solvents can also be applied to aqueous cyclopropanations with similar results. In situ generation of ethyl diazoacetate and cyclopropanation also proceeds efficiently. A chemoselective O-H insertion is also possible in water when hydrophobic catalysts and alcohols are used.
[反应：见正文] 在水介质中使用羧酸铑（II），涉及重氮乙酸乙酯和烯烃的环丙烷化反应以惊人的高效率进行。西山的钌（II）Py-盒配合物和胜木的钴（II）Salen配合物可在有机溶剂中实现高度对映选择性环丙烷化，也可应用于水相环丙烷化，且结果相似。重氮乙酸乙酯的原位生成和环丙烷化也能高效进行。当使用疏水催化剂和醇类时，在水中也可能发生化学选择性的O-H插入反应。
