Mechanism of the Regio- and Diastereoselective Ring Expansion Reaction Using Trimethylsilyldiazomethane

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• 作者：Takeo Sakai ; Satoshi Ito ; Hiroki Furuta ; Yuki Kawahara ; Yuji Mori
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 7, 2012
• 年：2012
• 卷：14
• 期：17
• 页码：4564-4567
• 全文大小：302K
• 年卷期：v.14,no.17(September 7, 2012)
• ISSN：1523-7052

文摘

An equatorial attack of TMS-diazomethane was determined to be the first step of the BF₃-promoted ring expansion reaction of six-membered ketones using TMS-diazomethane. The migration reaction occurred in a conformation in which the carbonyl oxygen and the TMS group were antiperiplanar to predominantly afford trans-seven-membered ketones.