Enantioselective synthesis of an atropisomeric diaryl ether

被引：56

作者：

Clayden, Jonathan ^{[1
]}

Worrall, Christopher P. ^{[1
]}

Moran, Wesley J. ^{[1
]}

Helliwell, Madeleine ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

atropisomerism; conformation analysis; diaryl ethers; sulfur;

D O I：

10.1002/anie.200705660

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C-O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3234 / 3237

页数：4

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