A Tandem Asymmetric Friedel-Crafts Alkylation/Michael Addition: Synthesis of Novel Ergoline Derivatives

被引：5

作者：

Connon, Robert ^{[1
]}

Guiry, Patrick J. ^{[1
,2
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Synth & Solid State Pharmaceut Ctr SSPC, Dublin 4, Ireland

[2] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 34期

基金：

爱尔兰科学基金会;

关键词：

Enantioselectivity; Catalysis; Tandem reaction; Ergoline; Oxazoline ligands; OXAZOLINE-CONTAINING LIGANDS; BIS(OXAZOLINE) LIGANDS; (+/-)-LYSERGIC ACID; INDOLES; NITROALKENES;

D O I：

10.1002/ejoc.201901007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the development of an asymmetric tandem Friedel-Crafts alkylation/Michael addition of 4-substituted indoles with trans-beta-nitrostyrene derivatives. By employing a chiral Zn-II-(bis)oxazoline catalyst we could control the formation of three contiguous chiral centers in one step in 57 %-99 % yield and up to > 99 % ee. This methodology provides easy access to a range of novel C-4-substituted products containing the tricyclic core of the ergoline skeleton and allows for the synthesis of tetracyclic ergoline derivatives with four chiral centers, in high enantioselectivity and as single isolated diastereomers.

引用

页码：5950 / 5954

页数：5

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