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Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone

Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone
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摘要 An unusual formal oxy transposition of vinylogous β-silyloxy-cyclobutanone 1(a 1,5-difunctionalized substrate) under mild acidic conditions(aqueous HF in CH3CN at 0℃) to the decalinic y-lactone 2 was described.A plausible mechanistic pathway involving the Grob-type fragmentation and intramolecularγ-Iactonization was proposed. An unusual formal oxy transposition of vinylogous β-silyloxy-cyclobutanone 1(a 1,5-difunctionalized substrate) under mild acidic conditions(aqueous HF in CH3CN at 0℃) to the decalinic y-lactone 2 was described.A plausible mechanistic pathway involving the Grob-type fragmentation and intramolecularγ-Iactonization was proposed.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2017年第5期968-970,共3页 中国化学快报(英文版)
基金 financial support from National Natural Science Foundation of China(NSFC,Nos.21302177,21672049 and 21672030)
关键词 Grob fragmentation Vinylogous β-silyloxy-cyclobutanone Decalinic γ-lactone Oxy transposition Intramolecular γ-lactonization Grob fragmentation Vinylogous β-silyloxy-cyclobutanone Decalinic γ-lactone Oxy transposition Intramolecular γ-lactonization
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