A novel strategy towards the asymmetric synthesis of orthogonally funtionalised 2-N-benzyl-N-alpha-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.
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.
Garrido
Narciso M
NM
Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain. nmg@usal.es
El Hammoumi
Mohamed M
MM
Díez
David
D
García
Mercedes
M
Urones
Julio G
JG
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D006868:Hydrolysis; D018020:Lithium Compounds / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
C524854:2-N-benzyl-N-alpha-methylbenzylamino-5-carboxymethylcyclopentane-1-carboxylic acid; D000596:Amino Acids; D002264:Carboxylic Acids; D003517:Cyclopentanes; D018020:Lithium Compounds; D014269:Trifluoroacetic Acid