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Asymmetric homologation of ketones. A new entry to orthogonally protected (2R,4R)-piperidine-2,4-dicarboxylic acid.

  作者 Etayo, Pablo;Badorrey, Ramon;Diaz-de-Villegas, Maria D.;Galvez, Jose A.;  
  选自 期刊  Journal of Organic Chemistry;  卷期  2008年73-21;  页码  8594-8597  
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[摘要]A new conformationally constrained analog of glutamic acid has been synthesized efficiently in seven steps from a chiral 2-alkyl-4-piperidone. The synthesis is based on the unprecedented asym. one-carbon homologation of the ketone controlled by the size of the N-substituent and the appropriate manipulation of substituents at positions 2 and 4 of the piperidine ring, a step that involves two independent oxidn. processes.

 
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