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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Solution-phase parallel synthesis of a multisubstituted cyclic imidate library
Saurabh Mehta1, Jesse P Waldo, Benjamin Neuenswander
1Department of Chemistry, Iowa State University , Ames, Iowa 50011, United States.
Abstract:
The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.
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