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Synthesis 2020; 52(08): 1215-1222
DOI: 10.1055/s-0039-1690241
DOI: 10.1055/s-0039-1690241
special topic
A Base-Promoted One-Pot Asymmetric Friedel–Crafts Alkylation/Michael Addition of 4-Substituted Indoles
This publication has emanated from research conducted (RC) with the financial support of the Synthesis and Solid State Pharmaceutical Centre (SSPC), funded by Science Foundation Ireland (SFI) under Grant No. 12\RC\2275) and is co-funded under the European Regional Development Fund under Grant No. 14/SP/2750. We acknowledge facilities provided by the Centre for Synthesis and Chemical Biology (CSCB) funded by the Higher Education Authority’s PRTLI.Further Information
Publication History
Received: 23 August 2019
Accepted after revision: 16 October 2019
Publication Date:
30 October 2019 (online)
Dedicated with respect and admiration to Professor Mark Lautens, a good friend and brilliant chemist, on the occasion of his 60th birthday.
Published as part of the Special Topic Domino C–H Functionalization/Cascade Catalysis
Abstract
Herein, we report a base-promoted Zn(II)–bis(oxazoline)-catalyzed one-pot Friedel–Crafts alkylation/Michael addition of 3-(indol-4-yl)acrylonitrile derivatives with trans-β-nitrostyrenes to yield the tricyclic core of the ergoline skeleton in up to 71% yield and 85% ee. During the purification of 3-(indol-4-yl)acrylonitrile, the key substrate for catalytic studies, a novel trans-cis-trans-cyclobutane derivative, thought to be formed via a [2+2] light-promoted cycloaddition, was identified by X-ray crystallographic analysis. Finally, a novel class of 4-substituted bis(indole)methane derivatives were serendipitously prepared in excellent yield by reacting 4-substituted indole derivatives with 4-nitrobenzaldehyde. One bis(indole)methane was characterized by X-ray crystallographic analysis.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690241.
- Supporting Information
- CIF File
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For examples of stereoselective domino reactions to synthesize 3,4-annulated indole scaffolds see:
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For the initial synthesis of bis(oxazoline) ligands of type L1 see:
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