Desymmetrisation of C-2-symmetric (2S,3S)-diazidobutane-1,4-diol with benzaldehyde
Scheurer A, Bauer W, Hampel F, Schmidt C, Saalfrank R, Mosset P, Puchta R, van Eikema Hommes N (2004)
Publication Status: Published
Publication Type: Journal article
Publication year: 2004
Journal
Publisher: Elsevier
Book Volume: 15
Pages Range: 867-872
Journal Issue: 5
DOI: 10.1016/j.tetasy.2004.01.027
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.
Authors with CRIS profile
Andreas Scheurer
Lehrstuhl für Anorganische und Allgemeine Chemie
Walter Bauer
Lehrstuhl für Organische Chemie II
Frank Hampel
Lehrstuhl für Organische Chemie I
Rolf Saalfrank
Naturwissenschaftliche Fakultät
Ralph Puchta
Naturwissenschaftliche Fakultät
Nicolaas van Eikema Hommes
Computer-Chemie-Centrum
Involved external institutions
France (FR)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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