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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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