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

Abstract

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