Asymmetric control in Diels–Alder cycloadditions of chiral 9-aminoanthracenes by relay of stereochemical information
作者:Harry Adams、Ramadan A. Bawa、Keith G. McMillan、Simon Jones
DOI:10.1016/j.tetasy.2007.04.012
日期:2007.5
cycloadditions with N-methyl maleimide and maleic anhydride. Excellent reactivity was achieved with good levels of diastereoselectivity, through a favourable combination of electrostatic and hydrogen bonding effects. Trial studies of the retro Diels–Alder reaction of these cycloadducts were also performed.
描述了两种合成手性9-氨基蒽的方法。首先,通过向BF 3 ·OEt 2促进的亚胺上亲核添加有机锂试剂,出乎意料地提供了稳定的氨基硼烷产品。第二种方法,使用钯催化的交叉偶联,对于伯胺而言更为成功,关键的9-(α-甲基苄基氨基)蒽与N-甲基马来酰亚胺和顺丁烯二酸酐进行环加成反应。通过静电和氢键作用的良好结合,以优异的非对映选择性实现了出色的反应性。还对这些环加合物的逆狄尔斯-阿尔德反应进行了试验研究。