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Synlett 1999; 1999(5): 632-634
DOI: 10.1055/s-1999-2662
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A New Diastereoselective Synthesis of Enantiomerically Pure 1,2-Oxazine Derivatives by Addition of Lithiated Methoxyallene to Chiral Nitrones

Wolfgang Schade* , Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Technischen Universität Dresden, D-01062 Dresden, Germany; Fax +49 35 14 63 70 30; E-mail: Hans.Reissig@chemie.tu-dresden.de
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Publication Date:
31 December 1999 (online)

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Addition of lithiated methoxyallene 2 to nitrones provided hydroxylamine derivatives which usually undergo very fast cyclization to 3,6-dihydro-2H-1,2-oxazines. Chiral nitrones 5, 8, or 10 which furnished 1,2-oxazines 6, 9, and 11 with excellent syn diastereoselectivities are of particular interest. By precomplexation of nitrone 5b with diethylaluminum chloride 1,2-oxazine 6b was produced with excellent anti selectivity. The resulting 3,5-dihydro-2H-1,2-oxazines are versatile starting materials for stereoselective syntheses of polyfunctional compounds.

methoxyallene - nitrone - allenyl hydroxylamine - 1,2-oxazine