A Tandem Cross-Metathesis/Semipinacol Rearrangement Reaction

作者:Plummer Christopher W; Soheili Arash; Leighton James L*
来源:Organic Letters, 2012, 14(10): 2462-2464.
DOI:10.1021/ol300691u

摘要

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-Grubbs 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.

  • 出版日期2012-5-18