Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides,Organic Chemistry Frontiers

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Catalytic enantioselective synthesis of indolizino[8,7-b]indole alkaloid derivatives based on the tandem reaction of tertiary enamides
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-12-10 , DOI: 10.1039/d0qo01147a
Xin-Ming Xu _{1,

2,

3,

4} , Ming Xie _{4,

5,

6,

7,

8} , Jiazhu Li _{1,

2,

3,

4} , Mei-Xiang Wang _{4,

5,

6,

7,

8}

Affiliation

An exquisite catalytic asymmetric tandem reaction of tertiary enamides catalyzed by a chiral Diph-Pybox/Cu(OTf)₂ complex was developed. The method, which comprised an enantioselective intramolecular addition of tertiary enamides to ketonic carbonyls followed by the diastereoselective interception of acyliminium by a tethered indole moiety, enables the expeditious synthesis of indolizino[8,7-b]indole derivatives with high yields, and excellent enantioselectivity and diastereoselectivity.

中文翻译：

基于叔酰胺类串联反应的吲哚并[8,7-b]吲哚生物碱衍生物的催化对映选择性合成

开发了一种精致的手性Diph-Pybox / Cu（OTf）_2配合物催化的叔酰胺类不对称串联反应。该方法包括将叔酰胺对映选择性分子内加到酮羰基上，然后通过束缚的吲哚部分非对映选择性地切断酰基亚胺，该方法可以快速合成高产率的吲哚并[8,7- b ]吲哚衍生物，并且具有出色的对映选择性和非对映选择性。

更新日期：2021-01-04

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