1998 pyridine derivatives

pyridine derivativesR 0380

45 - 152Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives.— Enantiomerically pure 4-piperidones, prepared by a recently developedasymmetric hetero Diels–Alder reaction, are used as starting materials for thesynthesis of the title compounds. The α-amino moiety is obtained by oxidationof a hydroxyl group or by using a furan ring as a masked carboxyl group. Thus,short procedures towards both D- and L-functionalized pipecolic acid derivativesare developed. Stereoselective epimerization of the α-carbon opens access toboth cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related todipeptide isosteres. — (BARLUENGA, J.; AZNAR, F.; VALDES, C.; RIBAS,C.; J. Org. Chem. 63 (1998) 12, 3918-3924; Inst. Quim. Organomet. ”EnriqueMoles”, Univ. Oviedo, E-33071 Oviedo, Spain; EN)

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1998 pyridine derivatives

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