Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

Chem Commun (Camb). 2011 Apr 7;47(13):3992-4. doi: 10.1039/c0cc05418f. Epub 2011 Feb 17.

Abstract

Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cinchona Alkaloids / chemistry
  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Nitroparaffins / chemistry*
  • Thiourea / chemistry*

Substances

  • Cinchona Alkaloids
  • Cyclohexanones
  • Nitro Compounds
  • Nitroparaffins
  • Thiourea
  • Methane
  • nitromethane