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Issue 11, 2020
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Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles

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Abstract

Medium-sized heterocycles exist in a broad spectrum of biologically active natural products and medicinally important synthetic compounds. The construction of medium-sized rings remains challenging, particularly the assembly of different ring sizes from the same type of substrate. Here we report palladium-catalyzed, regiodivergent [5 + 4] and [5 + 2] annulations of vinylethylene carbonates and allylidenemalononitriles. We describe the production of over 50 examples of nine- and seven-membered heterocycles in high isolated yields and excellent regioselectivities. We demonstrate the synthetic utility of this approach by converting a nine-membered ring product to an interesting polycyclic caged molecule via a [2 + 2] transannulation. Mechanistic studies suggest that the [5 + 2] annulation proceeds through palladium-catalyzed ring-opening/re-cyclization from the [5 + 4] adducts.

Graphical abstract: Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles

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Supplementary files

Article information


Submitted
17 Dec 2019
Accepted
09 Feb 2020
First published
10 Feb 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 2888-2894
Article type
Edge Article

Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles

X. Zhang, X. Li, J. Li, Q. Wang, W. Zou, Y. Liu, Z. Jia, F. Peng and B. Han, Chem. Sci., 2020, 11, 2888
DOI: 10.1039/C9SC06377C

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