Synthesis, Chromatographic Separation, Vibrational Circular Dichroism Spectroscopy, and ab Initio DFT Studies of Chiral Thiepane Tetraol Derivatives
The Journal of Organic Chemistry2004Vol. 70(2), pp. 664–669
Citations Over TimeTop 10% of 2004 papers
Vanda Cerè, Francesca Peri, Salvatore Pollicino, Alfredo Ricci, F. J. Devlin, Philip J. Stephens, Francesco Gasparrini, Romina Rompietti, Claudio Villani
Abstract
Optically pure enantiomers of the chiral tetrahydroxythiepane derivative 3,6-dihydroxy-4,5-O-isopropylidene-thiepane (3) are obtained using a novel protocol in which a library of all possible stereoisomers of 3 is synthesized, followed by two-step stereoselective chromatography, using, first, conventional achiral and, then, chiral stationary phases. Configurational and conformational analysis of 3 are carried out using Vibrational Circular Dichroism (VCD) spectroscopy in conjunction with ab initio DFT calculations. The absolute configuration of 3 is shown to be 3R,4S,5R,6R-(+)/3S,4R,5S,6S-(-).
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