Journal article


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


Publication Details
Author(s): Scheurer A, Bauer W, Hampel F, Schmidt C, Saalfrank R, Mosset P, Puchta R, van Eikema Hommes N
Publisher: Elsevier
Publication year: 2004
Volume: 15
Journal issue: 5
Pages range: 867-872
ISSN: 0957-4166

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 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. (C) 2004 Elsevier Ltd. All rights reserved.



How to cite
APA: Scheurer, A., Bauer, W., Hampel, F., Schmidt, C., Saalfrank, R., Mosset, P.,... van Eikema Hommes, N. (2004). Desymmetrisation of C-2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde. Tetrahedron-Asymmetry, 15(5), 867-872. https://dx.doi.org/10.1016/j.tetasy.2004.01.027

MLA: Scheurer, Andreas, et al. "Desymmetrisation of C-2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde." Tetrahedron-Asymmetry 15.5 (2004): 867-872.

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