Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara 630-0192, Japan.
J Org Chem. 2012 Mar 16;77(6):2911-23. doi: 10.1021/jo300201g. Epub 2012 Mar 7.
A highly efficient and accessible synthesis of chiral 3-substituted isoindolinone frameworks is described. The synthesis involved the Rh(I)-catalyzed asymmetric arylation of boronic acids to 2-halobenzaldimines and the subsequent Rh(I)-catalyzed intramolecular aminocarbonylation of the resulting 2-halobenzylamines using an aldehyde as the carbonyl source. The method tolerates a variety of functional groups, yielding isoindolinone derivatives in moderate to high yields with high ee-values. In addition, two Rh(I)-catalyzed transformations could be efficiently accomplished in a one-pot sequence to give chiral isoindolinones by the simple addition of a ligand and an aldehyde after the Rh(I)-catalyzed asymmetric arylation.
描述了一种高效且易于获得的手性 3-取代异吲哚啉酮骨架的合成方法。该合成涉及 Rh(I)催化的硼酸对 2-卤代苯亚胺的不对称芳基化反应，以及随后使用醛作为羰基源，所得 2-卤代苄胺的 Rh(I)催化的分子内氨基羰基化反应。该方法可以耐受多种官能团，以中等至高的收率和高对映选择性得到异吲哚啉酮衍生物。此外，通过在 Rh(I)催化的不对称芳基化反应后简单地添加配体和醛，两个 Rh(I)催化的转化可以在一锅序列中有效地完成，以通过简单的添加配体和醛，得到手性异吲哚啉酮。
