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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs
Leiyang Bai1, Bei Fu1, Xuefeng Jiang2
1Shanghai Key Laboratory of Green Chemistry and Chemical Process, Institute of Eco-Chongming, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China.
Abstract:
Here, we present an efficient protocol for stereoselective 4N-based domino dimerization in one single step, establishing a 22-membered library of asperazine A analogs. We describe steps for performing a gram-scale 2N-monomer to access the unsymmetrical 4N-dimer. We detail the synthesis of the desired dimer 3a as a yellow solid in 78% yield. This process demonstrates the 2-(iodomethyl)cyclopropane-1,1-dicarboxylate to be an iodine cation source. The protocol is limited to unprotected aniline of 2N-monomer. For complete details on the use and execution of this protocol, please refer to Bai et al. (2022).1.
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