A gold-triggered dearomative spirocarbocyclization/Diels-Alder reaction cascade towards diverse bridged N-heterocycles

A gold-triggered dearomative spirocarbocyclization/Diels-Alder reaction cascade towards diverse bridged N-heterocycles

A rapid approach for the diversity-oriented synthesis of complex bridged polycyclic N-heterocycles from readily available starting materials in two operational steps has been developed. This strategy firstly introduces molecular diversity by an Ugi four-component reaction, and then achieves these br...

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Veröffentlicht in:ORGANIC & BIOMOLECULAR CHEMISTRY 2019-11, Vol.17 (43), p.9529-9536
Hauptverfasser: He, Yi, Narmon, Thomas, Wu, Danjun, Li, Zhenghua, Van Meervelt, Luc, Van der Eycken, Erik V
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container_issue 43
container_start_page 9529
container_title ORGANIC & BIOMOLECULAR CHEMISTRY
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creator He, Yi
Narmon, Thomas
Wu, Danjun
Li, Zhenghua
Van Meervelt, Luc
Van der Eycken, Erik V
description A rapid approach for the diversity-oriented synthesis of complex bridged polycyclic N-heterocycles from readily available starting materials in two operational steps has been developed. This strategy firstly introduces molecular diversity by an Ugi four-component reaction, and then achieves these bridged N-heterocycles via an efficient gold-triggered chemo- and diastereoselective cascade non-oxidative ortho-dearomative spirocarbocyclization/Diels-Alder reaction sequence. The application of microwave irradiation for this cascade process efficiently shortens the reaction time to 10 minutes and improves the diastereoselectivity.
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title A gold-triggered dearomative spirocarbocyclization/Diels-Alder reaction cascade towards diverse bridged N-heterocycles
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