Activation of <i>N</i>-Sulfonyl Oxaziridines Using Copper(II) Catalysts: Aminohydroxylations of Styrenes and 1,3-Dienes
作者:David J. Michaelis、Michael A. Ischay、Tehshik P. Yoon
DOI:10.1021/ja800495r
日期:2008.5.1
N-Sulfonyloxaziridines are susceptible to electrophilic activation using copper(II) catalysts and react with styrenes under these conditions to provide 1,3-oxazolidines in a formal aminohydroxylation of the alkene. We propose a two-step mechanism involving a cationic intermediate to account for the rate differences and regioselectivities observed using a variety of styrenes. In accord with our hypothesis
N-磺酰基恶氮丙啶易于使用铜 (II) 催化剂进行亲电活化,并在这些条件下与苯乙烯反应以在烯烃的正式氨基羟基化中提供 1,3-恶唑烷。我们提出了一种涉及阳离子中间体的两步机制,以解释使用各种苯乙烯观察到的速率差异和区域选择性。根据我们的假设,一系列带有电子稳定基团的底物的氨基羟基化是成功的,1,3-二烯是铜(II)催化氨基羟基化的特别好的底物。不对称二烯的反应提供了良好到优异的烯烃选择性,考虑到我们的机制建议的阳离子中间体的稳定性,可以合理化其意义和大小。
Reaction of allyl bromides with bromoform and base under phase transfer conditions
作者:Mark S. Baird、Anthony G. W. Baxter、B. R. J. Devlin、R. J. G. Searle
DOI:10.1039/c39790000210
日期:——
The reaction of allylic bromides with bromoform and aqueous baseunderphasetransferconditions is strongly dependent on the catalyst; when benzyltriethylammonium chloride is used, the major primary product is a 4,4,4-tribromobut-1-ene.