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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Taming the reactive intermediates: the nazarov cyclization as a programmable platform
Yunfei Cheng1, Ye Yuan2, Qun Sun2
1School of Chemistry and Chemical Engineering, Huangshan University, Huangshan, 245061, China. 600127@hsu.edu.cn.
Abstract:
The Nazarov cyclization has evolved from a traditional acid-driven electrocyclization into a flexible synthetic platform. This review summarizes its transformation through a strategic framework centered on three control points: initiation, diverting, and stereochemistry. Modern initiation strategies (substrate pre‑activation, cooperative catalysis, photochemical excitation) replace harsh acids; diverting the oxyallyl cation delivers complex structures via intra‑ or intermolecular trapping; and stereochemical control ranges from chiral auxiliaries to novel catalytic systems. Key advances are illustrated through natural product syntheses.
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