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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to
Xianjun Xu1, Huangdi Feng2, Erik V Van der Eycken1,3
1Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium.
Abstract:
An efficient palladium-catalyzed reaction of N-propargyl oxazolidines for the construction of 4-substituted isoquinolines under microwave irradiation is developed. This transformation proceeds through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring. The practical value of this method has also been explored by conducting a millimole-scale reaction, as well as by transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.
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