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Molecules 2004, 9(5), 373-382; doi:10.3390/90500373
Article

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

* , , ,  and
Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain
* Author to whom correspondence should be addressed.
Received: 15 March 2004 / Revised: 24 March 2004 / Accepted: 24 March 2004 / Published: 30 April 2004
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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.
Keywords: Asymmetric synthesis; chiral lithium amide; β-amino acids; domino reaction; β-aminocyclopentane carboxilate; aminodiester orthogonal protection. Asymmetric synthesis; chiral lithium amide; β-amino acids; domino reaction; β-aminocyclopentane carboxilate; aminodiester orthogonal protection.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Garrido, N.M.; El Hammoumi, M.M.; Díez, D.; García, M.; Urones, J.G. A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.. Molecules 2004, 9, 373-382.

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