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以空气为终端氧化剂,钯(II)/铜(II)催化区域和立体选择性合成(E)-3-芳基亚甲基异吲哚啉-1-酮

Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of ( E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant.

作者信息

Youn So Won, Ko Tae Yun, Kim Young Ho, Kim Yun Ah

机构信息

Center for New Directions in Organic Synthesis, Department of Chemistry and Research Institute for Natural Sciences , Hanyang University , Seoul 04763 , Korea.

出版信息

Org Lett. 2018 Dec 21;20(24):7869-7874. doi: 10.1021/acs.orglett.8b03409. Epub 2018 Dec 4.

Abstract

Regio- and stereoselective synthesis of ( E)-3-arylmethyleneisoindolin-1-ones via Pd(II)/Cu(II)-catalyzed one-pot C-C/C-N bond forming sequence between amides and styrenes is reported. This method provides facile and rapid access to a diverse range of such compounds using readily available starting materials under mild aerobic conditions with good functional group tolerance and high selectivity and efficiency. Further elaboration of the products obtained from this process enabled very short and efficient syntheses of aristolactam and indoloisoquinolinone alkaloids.

摘要

报道了通过钯(II)/铜(II)催化酰胺与苯乙烯之间的一锅法C-C/C-N键形成序列实现(E)-3-芳基亚甲基异吲哚啉-1-酮的区域和立体选择性合成。该方法使用容易获得的起始原料,在温和的有氧条件下,以良好的官能团耐受性、高选择性和效率,提供了一种简便快捷地获得多种此类化合物的方法。对该过程所得产物的进一步衍生化能够非常简短且高效地合成马兜铃内酰胺和吲哚异喹啉酮生物碱。

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