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Synthesis 1996; 1996(1): 123-132
DOI: 10.1055/s-1996-4162
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Synthesis of Enantiopure 1,2-Didehydropyrrolidine, D-Proline, and Oxazoline Derivatives via Staudinger-Aza-Wittig Cyclization of γ-Azido Aldehydes

Johann Mulzer1 , Andreas Meier1 , Jürgen Buschmann2 , Peter Luger2
  • 1Institut für Organische Chemie der Johann-Wolfgang-Goethe Universität, Marie-Curie-Straße 11, D-60439 Frankfurt, Germany, Fax +49(69)79829464
  • 2Institut für Kristallographie der Freien Universität Berlin, Takustraße 6, D-14195 Berlin, Germany
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Publication Date:
31 December 2000 (online)

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The synthesis of 3-, 3,5- and 3,4,5-substituted prolines 1 and oxazolines 3 from inexpensive D-mannitol, employing the Staudinger-Aza-Wittig cyclization as a key step, is described.

peptidomimetics - Staudinger cyclization - oxazoline - cyanosilylation - cyclic imines