Journal
CHEMICAL SCIENCE
Volume 11, Issue 11, Pages 2888-2894Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc06377c
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Funding
- NSFC [21871031, 21702021, 81573588]
- Science & Technology Department of Sichuan Province [2017JQ0032, 2017JZYD0001, 2017JY0323]
- Thousand Talents Program of Sichuan Province
- Chengdu Talents Program
- Chengdu University
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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.
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