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Double Michael Addition of Oxindoles to Dienones Catalyzed by TBAB: An Efficient Route to Spirocyclic Oxindoles
Heterocycles ( IF 0.8 ) Pub Date : 2020-12-04 , DOI: 10.3987/com-20-14364
Hanfeng Cui , Jinxiang Zeng , Haiyong Cao , Yan Lin , Pingnan Wan , Wenqin Liu

The efficient synthesis of biologically active spiro compounds is a challenge for organic chemists and pharmaceutical chemists. Herein we describe a synthesis strategy of spirocyclic oxindoles via double Michael reaction of N-protected-oxindoles to dienones using tetrabutylammonium bromide (TBAB) as catalyst. The desired spirocyclic oxindoles were obtained with both high yields up to 99% and diastereoselectivity up to >95:5 dr.

中文翻译:

TBAB催化的二烯类化合物中双吲哚的双迈克尔加成反应:一种高效的制备螺环式氧化吲哚的途径

生物活性螺化合物的有效合成是有机化学家和药物化学家的挑战。在本文中,我们描述了通过使用四丁基溴化铵(TBAB)作为催化剂N-保护的羟吲哚与二烯酮的双迈克尔反应,合成螺环羟吲哚的合成策略。以高达99%的高收率和高达> 95:5 dr的非对映选择性获得了所需的螺环羟吲哚。
更新日期:2021-02-02
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