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A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.

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Author(s): Narciso M. Garrido | Mohamed M. El Hammoumi | David Díez | Mercedes García | Julio G. Urones

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 5;
Start page: 373;
Date: 2004;
Original page

Keywords: Asymmetric synthesis | chiral lithium amide | β-amino acids | domino reaction | β-aminocyclopentane carboxilate | aminodiester orthogonal protection.

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.
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