Rh(I)-Catalyzed Asymmetric Synthesis of 3-Substituted Isoindolinones through CO Gas-Free Aminocarbonylation

被引：51

作者：

Fujioka, Masahiko ^{[1
]}

Morimoto, Tsumoru ^{[1
]}

Tsumagari, Takayuki ^{[1
]}

Tanimoto, Hiroki ^{[1
]}

Nishiyama, Yasuhiro ^{[1
]}

Kakiuchi, Kiyomi ^{[1
]}

机构：

[1] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 06期

关键词：

FREE CARBONYLATIVE CYCLIZATION; CHIRAL DIENE LIGANDS; RHODIUM-CATALYZED ARYLATION; DIELS-ALDER REACTIONS; N-TOSYLARYLIMINES; HYDROFORMYLATION; FORMALDEHYDE; OLEFINS; EFFICIENT; ISOINDOLIN-1-ONES;

D O I：

10.1021/jo300201g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2911 / 2923

页数：13

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