Enantio- and periselective nitroalkene Diels-Alder reaction

Org Biomol Chem. 2012 Dec 14;10(46):9134-6. doi: 10.1039/c2ob26674a. Epub 2012 Oct 29.

Abstract

The periselective Diels-Alder reaction of 5-substituted pentamethylcyclopentadienes and nitroethylene has been realized by helical-chiral hydrogen bond donor catalysts. To our knowledge, this represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via activation of nitroalkene, and thus establishes its proof-of-principle.

Publication types

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

MeSH terms

  • Catalysis
  • Cycloaddition Reaction
  • Cyclopentanes / chemistry*
  • Ethylenes / chemistry*
  • Hydrogen Bonding
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Stereoisomerism

Substances

  • 1,2,3,4,5-pentamethyl-cyclopentadiene
  • Cyclopentanes
  • Ethylenes
  • Nitro Compounds