Asymmetric synthesis of 3,4-diaminocyclohexanol and endo-7-azabicyclo[2.2.1]heptan-2-amine

Org Lett. 2010 Nov 5;12(21):4964-7. doi: 10.1021/ol102103y.

Abstract

Hydroboration of (1R,2R)-bis[(S)-1-phenylethylamino]cyclohex-4-ene and its derivatives with several borane reagents gave diastereomeric mixtures of the 3,4-diaminocyclohexanol derivatives. Cyclization of the prevalent diastereomer with the R configuration of the newly formed stereocenter under Mitsunobu conditions, followed by reductive removal of the N-substituents, gave the optically pure endo-7-azabicyclo[2.2.1]heptane-2-amine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Cyclohexanols / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • 3,4-diaminocyclohexanol
  • 7-azabicyclo(2.2.1)heptane
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cyclohexanols