Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal, MP-462 066, India.
Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur, UP-208 016, India.
Org Lett. 2017 Feb 3;19(3):476-479. doi: 10.1021/acs.orglett.6b03623. Epub 2017 Jan 11.
An efficient route to pharmacologically interesting isoindolinone-based α-amino phosphonates is described via asymmetric hydrophosphonylation of in situ generated ketimines catalyzed by BINOL-derived phosphoric acid. The reaction proceeds smoothly at ambient temperature affording a variety of α-amino phosphonates with a quaternary stereogenic center embedded in isoindolinone motif in high yields with excellent enantiomeric ratios (up to 98.5:1.5 er). Several interesting transformations of the products into valuable synthetic intermediates are also depicted.
描述了一种通过手性联萘酚衍生的磷酸催化原位生成的亚胺的不对称氢膦酰化反应来制备具有药理活性的异吲哚啉酮基α-氨基膦酸酯的有效途径。该反应在环境温度下顺利进行，以高收率和优异的对映体比值（高达 98.5:1.5 er）提供了多种在异吲哚啉酮骨架中嵌入季立体中心的α-氨基膦酸酯。还描绘了产物转化为有价值的合成中间体的几种有趣的转化。
