𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Optically active telluronium imides: Optical resolution, absolute configuration, and mechanism of racemization

✍ Scribed by Toshio Shimizu; Yoshito Machida; Nobumasa Kamigata

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
119 KB
Volume
14
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Thermodynamically and kinetically stabilized asymmetric diaryltelluronium imides were synthesized and optically resolved into their enantiomers on an optically active column using medium‐pressure column chromatography. The relationship between the absolute configuration and the optical properties of the chiral telluronium imides was clarified. The mechanism of the racemization, which involves the formation of telluroxides by the hydrolysis of the telluronium imides, was proposed. Β© 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:523–529, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10185

πŸ“œ SIMILAR VOLUMES

Optical resolution and absolute configur
Optical resolution and absolute configuration of N-Benzyloxycarbonyl-Ξ±-alkoxyglycines
✍ Masao Kawai; Keiichi Yamada; Kouji Hosoda; Yasuhiro Omori; Shuji Kato; Nobuhiro πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 129 KB πŸ‘ 1 views

Optical resolution of racemic N-benzyloxycarbonyl-protected alpha-alkoxyglycines, (+/-)-Cbz-Gly(OR)-OH (R = Et and Pr(i)), was achieved by means of fractional crystallization of diastereomeric salts with (+)-(1S,2S)-2-amino-1-phenyl-1,3-propanediol or diastereomeric esters of (+)- or (-)-menthol. Th

Preparation and configuration of racemic
Preparation and configuration of racemic and optically active analgesic cycloaminoalkylnaphthalenes
✍ Victor Ghislandi; Simona Collina; Ornella Azzolina; Annalisa Barbieri; Enrica La πŸ“‚ Article πŸ“… 1999 πŸ› John Wiley and Sons 🌐 English βš– 189 KB

Cycloaminoalkylnaphthalene 3 shows interesting opioid-like analgesic properties. It possesses two chiral centers and can exist as two racemic pairs and four diastereomers. Since the binding of opioids with receptors is stereoselective, it was important to have the two racemic pairs as well as the fo