Abstract
Abstract The syntheses and resolutions of enantiomerically enriched 4-phenyl, 4-tert-butyl, and 4-isopropyl pipecolic acids are described. Optically active diastereomers were prepared by diastereomeric salt formation with the chiral base, l -tyrosine hydrazide, to provide Cbz or Boc protected 4-cis- d -pipecolic acid derivatives in >98% ee. Subsequent esterification followed by sodium methoxide catalyzed epimerization provided the isomeric 4-trans- l -pipecolic esters. In addition, an efficient synthesis of 4-phenyl-cis-pipecolic acid is described.
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