Desymmetrisation of C-2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde

作者：Scheurer A^*; Bauer W; Hampel F; Schmidt C; Saalfrank RW; Mosset P; Puchta R; Hommes NJRV

来源：Tetrahedron: Asymmetry , 2004, 15(5): 867-872.

DOI：10.1016/j.tetasy.2004.01.027

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 C-2-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.

• 出版日期2004-3-8