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Issue 77, 2020

Synthesis of polycyclic indoles via organocatalytic bicyclization of α-alkynylnaphthalen-2-ols with nitrones

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Abstract

A new organocatalytic bicyclization of α-alkynylnaphthalen-2-ols with nitrones was first reported, leading to the convergent synthesis of polycyclic indoles with substantial substitution diversity in generally good yields through scission of the N–O bond of nitrones via [3,3]-sigmatropic rearrangement. This transformation showcases the use of a quinine catalyst in a complicated cascade system that has been shown to effectively construct polycyclic heterocycles via alkyne difunctionalization.

Graphical abstract: Synthesis of polycyclic indoles via organocatalytic bicyclization of α-alkynylnaphthalen-2-ols with nitrones

Supplementary files

Article information


Submitted
22 Jul 2020
Accepted
19 Aug 2020
First published
19 Aug 2020

Chem. Commun., 2020,56, 11406-11409
Article type
Communication

Synthesis of polycyclic indoles via organocatalytic bicyclization of α-alkynylnaphthalen-2-ols with nitrones

T. Xu, N. Lin, W. Hao, J. Zhang, M. Li, S. Tu and B. Jiang, Chem. Commun., 2020, 56, 11406 DOI: 10.1039/D0CC05027J

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