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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Bi-Catalyzed [3 + 2] Cycloaddition of C2-Spirocyclopropyl-indolin-3-ones with Carbonyls: Access to
Ming-Liang Rao1, Mao Zhang1, Jia-Hao He1
1State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, School of Pharmaceutical Sciences, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 561113, P. R. China.
Abstract:
Herein, the first Bi-catalyzed [3 + 2] cycloaddition of C2-spirocyclopropyl-indolin-3-ones and carbonyl compounds has been developed under mild conditions, enabling efficient and diastereoselective access to multisubstituted spiro[furan-3,2'-indolin]-3'-ones (73 examples, up to 91% yield, >20:1 dr). This transformation employs C2-spirocyclopropyl-indolin-3-ones as C3 synthons and exhibits broad substrate tolerance, accommodating various aromatic aldehydes, α,β-unsaturated aldehydes, aliphatic aldehydes, and even challenging ketones.
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