A New Diastereoselective Synthesis of Enantiomerically Pure 1,2-Oxazine Derivatives by Addition of Lithiated Methoxyallene to Chiral Nitrones

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Abstract
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.

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