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

doi:10.3390/90500373

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

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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.

Narciso M. Garrido * , Mohamed M. El Hammoumi, David Díez, Mercedes García and Julio G. Urones

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; in revised form: 24 March 2004 / Accepted: 24 March 2004 / Published: 30 April 2004

(This article belongs to the Special Issue Carbanion chemistry from Carboxylic acids in honor of Prof. Ramón Mestres on his 65th anniversary)

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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.

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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.

AMA 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(5):373-382.

Chicago/Turabian Style

Garrido, Narciso M.; El Hammoumi, Mohamed M.; Díez, David; García, Mercedes; Urones, Julio G. 2004. "A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.." Molecules 9, no. 5: 373-382.

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