Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and a initio DFT studies of chiral thiepane tetraol derivatives

被引:42
作者
Cerè, V
Peri, F
Pollicino, S
Ricci, A
Devlin, FJ
Stephens, PJ
Gasparrini, F
Rompietti, R
Villani, C
机构
[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
[2] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[3] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, I-00185 Rome, Italy
关键词
D O I
10.1021/jo048629y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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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页码:664 / 669
页数:6
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