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Issue 98, 2019
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Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

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Abstract

A Lewis acid-catalyzed insertion of unsymmetrical alkynes into electron-deficient alkenes was developed for the first time, and used to produce 34 hitherto unreported pentacyclic benzo[5,6]chromeno[2,3-b]indoles with generally good yields and complete stereoselectivity. A Yb(OTf)3-catalyzed reaction between o-alkynylnaphthols and 3-methyleneindolin-2-ones proceeded efficiently, and provided a simple and convergent protocol for alkyne difunctionalization via oxidant-free C–C double bond breaking/rearrangement. Mechanistic details of this domino process were derived by conducting systematic theoretical calculations.

Graphical abstract: Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

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Publication details

The article was received on 09 Nov 2019, accepted on 18 Nov 2019 and first published on 18 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC08762A
Chem. Commun., 2019,55, 14757-14760

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    Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

    K. Chen, T. Xu, J. Liang, M. Zhou, J. Zhang, W. Hao, J. Wang, S. Tu and B. Jiang, Chem. Commun., 2019, 55, 14757
    DOI: 10.1039/C9CC08762A

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