A. Scheurer, W. Bauer, F. Hampel
Mar 8, 2004
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Tetrahedron-asymmetry
Abstract
Abstract Surprisingly, doubly functionalised (2S,3S)-diazidobutane-1,4-diol under modified Boyer conditions reacted with only 1 equiv of benzaldehyde yielding a mono oxazoline, whereas quantum chemical studies favour the formation of the C2-symmetric bioxazoline. In addition, the oxazoline formation was indirectly confirmed via detailed NMR studies and X-ray structure analysis of the oxazoline p-nitrobenzoic acid ester derivative.