Homologous Mukaiyama reactions via trapping of the Nazarov intermediate with silyloxyalkenes

Org Lett. 2011 Jul 15;13(14):3584-7. doi: 10.1021/ol201125h. Epub 2011 Jun 23.

Abstract

Treatment of 1,4-pentadien-3-ones and silyloxyalkenes with BF(3)·OEt(2) at room temperature or lower initiates a domino process consisting of sequential 4π electrocyclization and capture of the resulting cyclopentenyl cation by the electron-rich trap. The overall process furnishes 1,4-dicarbonyl products containing highly substituted cyclopentanones in good yields and with the establishment of up to five new stereocenters.