Versatile [3 + 2] methylenecyclopentane annulations of unactivated and electron-rich olefins with [(trimethylsilyl)methylene]cyclopropanedicarboxylates Academic Article uri icon

abstract

  • [(Trimethylsilyl)methylene]cyclopropanedicarboxylates 8a-c are readily available from the cyclopropanation of the silylallenes 7a-c with dimethyl diazomalonate. The free-radical mediated methylenecyclopentane annulations of unactivated and electron-rich alkenes with 8a-c proceed in high yield. The product vinylsilans are set up for diverse secondary conversions, making annulations with 8a-c highly versatile in the synthesis of cyclopentanes. © 1994, American Chemical Society. All rights reserved.

author list (cited authors)

  • Huval, C. C., & Singleton, D. A.

citation count

  • 42

publication date

  • April 1994