Development of New Synthetic Methods of Heterocycles Using Chloramine‐T as a Nitrogen Source
Development of New Synthetic Methods of Heterocycles Using Chloramine‐T as a Nitrogen Source
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以氯胺-T为氮源的杂环合成新方法的发展
DOI：
10.1002/chin.200348248
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发表时间：
2003
期刊：
影响因子：
--
通讯作者：
M. Komatsu
中科院分区：
文献类型：
--
作者：
S. Minakata;M. Komatsu
我们开发了以氯胺-T为N1单元构建N-杂环的新策略。研究发现，氯化铜或碘是氯胺-T催化各种烯烃叠氮化反应的良好催化剂。氯胺-T和硝酸银的结合不仅直接从包括ƒ？，ƒ？-不饱和羰基化合物在内的烯烃中得到氮杂环丙烷，而且还从1，6-二烯中得到双环吡咯烷。以烯基碘和氯胺-T为原料，利用底物上的碘基团进行环化反应，实现了吡咯烷类化合物的高效立体选择性合成。此外，在相转移催化条件下或在二氧化硅和水的反应介质中，利用氯胺-T-I2体系实现了烯烃的有机无溶剂氮杂化反应。
We have exploited the novel strategies for construction of N-heterocycles using Chloramine-T as an N 1 unit. Copper(I) chloride or iodine was found to be a good catalyst for aziridination of various alkenes with Chloramine-T. The combination of Chloramine-T and silver nitrate directly led to not only aziridines from alkenes including ƒ¿, ƒÀ-unsaturated carbonyl compounds but also bicyclic pyrrolidines from 1, 6-dienes. The synthesis of pyrrolidine derivatives was achieved efficiently and stereoselectively from alkenyl iodides and Chloramine-T, in which the iodo group of the substrates has multiple functions to perform the cyclization. Furthermore, organic-solvent-free aziridination of alkenes was developed by utilizing Chloramine-T-I2 system under phase-transfer catalyst conditions or under the reaction media of silica and water.