EPIMERIZATION OF TRANS-3-ARYLAZIRIDINE-2-CARBOXYLATES AT THE C3 POSITION
EPIMERIZATION OF TRANS-3-ARYLAZIRIDINE-2-CARBOXYLATES AT THE C3 POSITION
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DOI：
10.3987/com-08-s(n)74
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发表时间：
2008-11-01
期刊：
影响因子：
0.6
通讯作者：
Ishikawa, Tsutomu
中科院分区：
文献类型：
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作者：
Kumamoto, Takuya;Nagayama, Shin-ichiro;Ishikawa, Tsutomu
我们描述了1-苄基-3-芳基氮杂环丙烷-2-羧酸酯的反式异构体的有效异构化。金属钐、碘和N，N-二甲氨基乙醇的结合促进了反式异构体的异构化为顺式和反式异构体的约1：1混合。在研究更有效的催化剂时，发现氯化铟提供了大约2：1的顺式和反式异构体的混合物。从光学活性的结果可以推测氮杂环丙烷的苯基位置上的表观异构化。在此异构化反应中，实现了顺-2-吲哚氮杂氮杂环丙烷的合成，构建了氮杂环氧丙烷骨架。
We describe here effective epimerization of trans to cis isomer of 1-benzyl-3-arylaziridine-2-carboxylates. The combination of samarium metal, iodine and N,N-dimethylaminoethanol promoted the epimerization of trans isomer to a ca. 1 : 1 mixture of cis and trans ones. Investigating more effective catalyst, indium chloride was found to afford a ca. 2 : 1 mixture of cis and trans isomers. Epimerization at benzylic position in the aziridines is suggested from the result with optically active ones. Preparation of cis-2-indolylaziridine towards construction of aziridinomitosene skeleton was achieved in this epimerization reaction.