An Organocatalytic Synthesis of cis-N-Alkyl- and N-Arylaziridine Carboxylates
An Organocatalytic Synthesis of cis-N-Alkyl- and N-Arylaziridine Carboxylates
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DOI：
10.1002/adsc.200900474
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发表时间：
2009-11-01
影响因子：
5.4
通讯作者：
Pesce, Paolo
中科院分区：
文献类型：
--
作者：
Bew, Sean P.;Carrington, Rachel;Pesce, Paolo
一个非常温和的方案，采用容易获得的起始材料，即，醛、胺和重氮基乙酸烷基酯，当掺入三氟甲磺酸吡啶鎓作为有机催化剂时，以优异的产率和立体选择性返回结构上不同的N-取代的-C-2/3-双官能化氮丙啶。反应过程是环境友好的，提供水和氮气作为唯一的副产物。该外消旋方案为开发能够产生光学活性氮杂环丙烷的新型不对称有机催化剂铺平了道路。
An extremely mild protocol that employs readily available starting materials, i.e., aldehyde, amine and alkyl diazoacetate, returns structurally diverse N-substituted-C-2/3-difunctionalised aziridines in excellent yields and stereoselectivities when pyridinium triflate is incorporated as an organocatalyst. The reaction process is environmentally benign affording water and nitrogen as the only by-products. This racemic protocol paves the way for the development of novel asymmetric organocatalysts capable of generating optically active aziridines.