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

作　　者：Xiang Wu Wei-Dong Z.Li 

机构地区：[1]School of Chemistry and Chemical Engineering,Hefei University of Technology [2]Innovative Drug Research Centre,Chongqing University

出　　处：《Chinese Chemical Letters》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)

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.

关 键 词：Grob fragmentation Vinylogous β-silyloxy-cyclobutanone Decalinic γ-lactone Oxy transposition Intramolecular γ-lactonization 

分 类 号：O624.5[理学—有机化学]