A novel strategy towards the asymmetric synthesis of orthogonally funtionalised 2-N-benzyl-N-alpha-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid |
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| Authors: | Garrido Narciso M El Hammoumi Mohamed M Díez David García Mercedes Urones Julio G |
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| Institution: | Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain. nmg@usal.es |
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| Abstract: | The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-alpha-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-alpha-methylbenzylamino-5-carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-alpha-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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