Catalytic Dual 1,1-H-Abstraction/Insertion for Domino Spirocyclizations

J Am Chem Soc. 2015 Jul 22;137(28):8928-31. doi: 10.1021/jacs.5b05735. Epub 2015 Jul 8.

Abstract

A catalytic domino spirocyclization of 1,7-enynes with simple cycloalkanes and cyclo-1,3-dicarbonyls has been established via multiple C-C bond formations from alkynyl/alkenyl functions and dual α,α-C(sp(3))-H abstraction/insertion. The reaction involves addition, 6-exo-dig cyclization and radical coupling sequences under convenient catalytic conditions and provides a concise access to spiro cyclopenta[c]quinolines in good to excellent yields.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkanes / chemical synthesis
  • Alkanes / chemistry
  • Catalysis
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry
  • Models, Molecular
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkanes
  • Cyclopentanes
  • Quinolines
  • Spiro Compounds