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

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• 作者：Masahiko Fujioka ; Tsumoru Morimoto ; Takayuki Tsumagari ; Hiroki Tanimoto ; Yasuhiro Nishiyama ; Kiyomi Kakiuchi
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：March 16, 2012
• 年：2012
• 卷：77
• 期：6
• 页码：2911-2923
• 全文大小：490K
• 年卷期：v.77,no.6(March 16, 2012)
• ISSN：1520-6904

文摘

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.