A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-ÃŽÂ±-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.Author(s): Narciso M. Garrido | Mohamed M. El Hammoumi | David DÃƒÂez | Mercedes GarcÃƒÂa | Julio G. Urones
Journal: Molecules ISSN 1420-3049
Volume: 9; Issue: 5; Start page: 373; Date: 2004;
Keywords: Asymmetric synthesis | chiral lithium amide | ÃŽÂ²-amino acids | domino reaction | ÃŽÂ²-aminocyclopentane carboxilate | aminodiester orthogonal protection.
The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-ÃŽÂ±-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-ÃŽÂ±-methylbenzylamino-5Ã¢Â€Â“carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-ÃŽÂ±-methylbenzyl-N-benzylamide initiated by a Michael addition, subsequent 5-exo-trig intramolecular cyclisation and posterior selective hydrolysis with trifluoroacetic acid is reported.