5-Carboxy-2-azabicyclo[2.1.1]hexanes as precursors of 5-halo, amino, phenyl, and 2-methoxycarbonylethyl methanopyrrolidines

J Org Chem. 2006 Mar 3;71(5):2090-8. doi: 10.1021/jo052506b.

Abstract

Novel 5-X-substituted-2-azabicyclo[2.1.1]hexanes (X = 5-syn-Cl, -Br, -I, -Ph, -NHCOOR (R = Me, Bn, t-Bu), -CH2CH2COOMe and X = 5-anti-Br, -I, -Ph) were synthesized from the X = 5-syn-carboxy derivative. New 5-anti-X-2-azabicyclo[2.1.1]hexanes, X = NHCOOR (R = Me, Bn), were prepared stereoselectively from the X = 5-anti-carboxy substrate.

Publication types

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

MeSH terms

  • Acids / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Esters
  • Hexanes / chemical synthesis
  • Hexanes / chemistry*
  • Iodides / chemistry
  • Oxidants / chemistry
  • Pyrrolidines / chemical synthesis*
  • Stereoisomerism

Substances

  • Acids
  • Bridged Bicyclo Compounds, Heterocyclic
  • Esters
  • Hexanes
  • Iodides
  • Oxidants
  • Pyrrolidines