肟醚碳负离子对氮杂环丙烷的开环反应

Ring-opening Reaction of Aziridines with α-Carbanion of Oximes

在添加六甲基膦酰胺(HMPA)的条件下,实现了苯乙酮肟醚α-碳负离子对单取代和环状氮杂环丙烷的开环,取得中等到良好的收率.四氢萘酮肟醚α-碳负离子在该条件下也可对部分氮杂环丙烷进行开环反应.反应中HMPA对锂离子发生络合作用,在一定程度上增加碳负离子的亲核性.

Aziridine is a very useful synthetic intermediate in organic synthesis.The ring-opening reaction of aziridine with various heteroatom nucleophiles has received intensive attention by organic chemists.However,the development of using carbon nucleophiles,especially unstablized carbon nucleophiles,falls far behind.In this regard,we reported ring-opening reaction of α-carbanion of acetophenone oxime with aziridines in the presence of HMPA,affording corresponding products in moderate to good yields.Tetralone oxime is also a suitable substrate for some monosubstituted aziridines.This method offers a new example of the ring-opening reaction of carbanion with aziridines.