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-(-)
Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and ab initio dft studies of chiral thiepane tetraol derivatives / V., Cere'; F., Peri; S., Pollicino; A., Ricci; F. J., Devlin; P. J., Stephens; Gasparrini, Francesco; R., Rompietti; Villani, Claudio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 70:(2005), pp. 664-669. [10.1021/jo048629y]
Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and ab initio dft studies of chiral thiepane tetraol derivatives
GASPARRINI, Francesco;VILLANI, Claudio
2005
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-(-)I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
