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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

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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