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

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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)

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.

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 NM, El Hammoumi MM, Díez D, García M, Urones JG. 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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