The bronsted acid-catalyzed direct aza-darzens synthesis of N-alkyl cis-aziridines
The bronsted acid-catalyzed direct aza-darzens synthesis of N-alkyl cis-aziridines
复制标题
DOI：
10.1021/ja0385282
复制
发表时间：
2004-02-18
影响因子：
15
通讯作者：
Johnston, JN
中科院分区：
文献类型：
--
作者：
Williams, AL;Johnston, JN
介绍了一种温和的合成顺式氮杂环醚的方法，该方法采用一定量的硼酸作为催化剂。尽管暴露于质子源时，重氮化合物可能通过烷基化或均偶联进行分解，但相对于席夫碱存在时的[2 + 1]环化，这些途径是缓慢的，从而导致叠氮产物。该工艺不使用必须用色谱法去除的金属或试剂，具有快速的周转率，并且只产生原子氮作为副产物。当手性非外消旋醛形成席夫碱时，高水平的相对立体控制也是可能的。
A mild protocol for the synthesis ofcis-aziridines is described that employs a catalytic amount of Brønsted acid. Despite the potential for diazo compound decomposition via alkylation or homocoupling upon exposure to a proton source, these pathways are slow relative to [2 + 1] annulation in the presence of a Schiff base, leading to aziridine product. The process uses no metals or reagents that must be removed chromatographically, exhibits rapid turnover rates, and produces only atomic nitrogen as a coproduct. High levels of relative stereocontrol are also possible when forming the Schiff base from a chiral nonracemic aldehyde.