Synthesis 2000; 2000(14): 2051-2059
DOI: 10.1055/s-2000-8719
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Asymmetric Synthesis of 2-(α-Aminoalkyl)oxazoles, 2-Oxazolylpyrrolidines, 2-Oxazolylpiperidines: Total Synthesis of 4,5-Dihydroxypipecolinic Acid

Marion Thieme* , Eric Vieira, Jürgen Liebscher
  • *Institut für Chemie, Humboldt-Universität Berlin, Hessische Straße 1-2, D-10115 Berlin, Germany; Fax +49(30)20 93 89 07; E-mail: [email protected]
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31. Dezember 2000 (online)

Asymmetric α-alkylation of 2-aminomethyl-4,5-diphenyloxazole was achieved by formation of azomethines 1 and ent-1 with the enantiomers of 2-hydroxypinan-3-one as chiral auxiliaries, reaction with alkylating reagents and final removal of the chiral auxiliary giving rise to optically active 2-(α-aminoalkyl)oxazoles 3, ent-3, 6 and 9. If α,ω-dihaloalkanes were used the resulting alkylation products could be further cyclized by intramolecular alkylation of the amino group to afford optically active 2-oxazolyl-N-heterocycles 4, ent-4, 7 and 10. The latter could be used for the total synthesis of naturally occurring 4,5-dihydroxypipecolinic acid 13.