Journal of the American Chemical Society

A new approach to the Nazarov reaction via sequential electrocyclic ring opening and ring closure

TN Grant, FG West

文献索引：Grant, Tina N.; West Journal of the American Chemical Society, 2006 , vol. 128, # 29 p. 9348 - 9349

被引用次数: 65

摘要

Regioselective dichlorocyclopropanation of 2-silyloxydienes furnishes vinylcyclopropanol silyl ethers in good yield. Treatment with silver (I) at room temperature effects disrotatory electrocyclic opening to a 2-chloro-3-silyloxypentadienyl cation, which then undergoes conrotatory (Nazarov) electrocyclization to provide chlorocyclopentenones. This two-step sequence offers a convenient and mild alternative to the standard Nazarov cyclization ...

~82%

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