Asymmetric Amidoselenenylation of Alkenes Promoted by Camphorselenenyl Sulfate: A Useful Synthetic Route to Enantiopure Oxazolines
作者:Marcello Tiecco、Lorenzo Testaferri、Claudio Santi、Cristina Tomassini、Francesca Marini、Luana Bagnoli、Andrea Temperini
DOI:10.1002/1099-0690(200010)2000:20<3451::aid-ejoc3451>3.0.co;2-q
日期:2000.10
Camphorselenenyl sulfate is an efficient chiral, nonracemic electrophilic reagent which can be produced from the easily available camphor diselenide by treatment with ammonium persulfate. This electrophilic selenium reagent reacts with alkenes, at room temperature in acetonitrile, in the presence of water and trifluoromethanesulfonic acid to afford the amidoselenenylation products with moderate facial
樟脑二硒基硫酸盐是一种有效的手性、非外消旋亲电试剂,可通过过硫酸铵处理从容易获得的樟脑二硒化物制备。这种亲电子硒试剂在室温下在乙腈中,在水和三氟甲磺酸存在下与烯烃反应,以提供具有中等表面选择性的酰胺硒烯基化产物。然而,两种非对映加成产物很容易分离。在用苯基硒基三氟甲磺酸酯或 SO2Cl2 活化硒部分后,这些产物通过分子内取代立体特异性地脱硒并提供对映体纯的恶唑啉。