Issue 14, 1986

An interpretation of the diastereofacial reactivity of (E)-3-trimethylsilyloxybuta-1,3-dien-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside based upon the exo-anomeric effect

Abstract

The geometry of the title diene has been probed by X-ray crystallography and by nuclear Overhauser effect difference spectroscopy; its diastereofacial discrimination in cycloadditions is ascribed to a reacting conformation determined by the exo-anomeric effect.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1986, 1116-1118

An interpretation of the diastereofacial reactivity of (E)-3-trimethylsilyloxybuta-1,3-dien-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside based upon the exo-anomeric effect

R. C. Gupta, A. M. Z. Slawin, R. J. Stoodley and D. J. Williams, J. Chem. Soc., Chem. Commun., 1986, 1116 DOI: 10.1039/C39860001116

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