A Tandem Cross-Metathesis/Semipinacol Rearrangement Reaction

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• 作者：Christopher W. Plummer ; Arash Soheili ; James L. Leighton
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：May 18, 2012
• 年：2012
• 卷：14
• 期：10
• 页码：2462-2464
• 全文大小：243K
• 年卷期：v.14,no.10(May 18, 2012)
• ISSN：1523-7052

文摘

An efficient and (E)-selective synthesis of a 6-alkylidenebicyclo[3.2.1]octan-8-one has been developed. The key step is a tandem cross-metathesis/semipinacol rearrangement reaction, wherein the Hoveyda鈥揋rubbs II catalyst, or more likely a derivative thereof, serves as the Lewis acid for the rearrangement. Despite the fact that both the starting alkene and the cross-metathesis product are viable rearrangement substrates, only the latter rearranges, suggesting that the Lewis acidic species is generated only after the cross-metathesis reaction is complete.