A novel strategy towards the asymmetric synthesis of orthogonally funtionalised 2-N-benzyl-N-alpha-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid

Molecules. 2004 Apr 30;9(5):373-82. doi: 10.3390/90500373.

Abstract

The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-alpha-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-alpha-methylbenzylamino-5-carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-alpha-methylbenzyl-N-benzylamide initiated by a Michael addition, subsequent 5-exo-trig intramolecular cyclisation and posterior selective hydrolysis with trifluoroacetic acid is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry*
  • Cyclization
  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / chemistry*
  • Hydrolysis
  • Lithium Compounds / chemistry
  • Models, Chemical
  • Molecular Structure
  • Stereoisomerism
  • Trifluoroacetic Acid / chemistry

Substances

  • 2-N-benzyl-N-alpha-methylbenzylamino-5-carboxymethylcyclopentane-1-carboxylic acid
  • Amino Acids
  • Carboxylic Acids
  • Cyclopentanes
  • Lithium Compounds
  • Trifluoroacetic Acid