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

Molecules

Narciso M. Garrido¹  Mohamed M. El Hammoumi²  David Dໞz²  Mercedes Garc໚² 

[1] id="af1-molecules-09-00373">Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain. Tel. [phone], Fax [phone]

关键词: Asymmetric synthesis;    chiral lithium amide;    β-amino acids;    domino reaction;    β-aminocyclopentane carboxilate;    aminodiester orthogonal protection;   

DOI  :  10.3390/90500373

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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