Li Hao, Song Feijie, Widenhoefer Ross A
Duke University, French Family Science Center, Durham, North Carolina, USA. ; Tel: +1-919-660-1533.
Adv Synth Catal. 2011 Apr 18;353(6):955-962. doi: 10.1002/adsc.201000844.
Treatment of N-allylic,N'-aryl ureas with a catalytic 1:1 mixture of di-tert-butyl-o-biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol %) in chloroform at room temperature led to 5-exo hydroamination to form the corresponding imidazolidin-2-ones in excellent yield. In the case of N-allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)-catalyzed 5-exo hydroamination leads to formation of the corresponding trans-3,4-disubstituted imidazolidin-2-ones in excellent yield with ≥50:1 diastereoselectivity.
在室温下,将N-烯丙基、N'-芳基脲与二-叔丁基-邻-联苯膦金(I)氯化物和六氟磷酸银的催化1:1混合物(1摩尔%)在氯仿中反应,会发生5-外向氢胺化反应,以优异的产率生成相应的咪唑啉-2-酮。对于具有烯丙基烷基、苄氧基甲基或乙酰氧基甲基取代基的N-烯丙基脲,金(I)催化的5-外向氢胺化反应会以优异的产率生成相应的反式-3,4-二取代咪唑啉-2-酮,非对映选择性≥50:1。