Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes

被引：116

作者：

Augustin, Andre U. ^{[1
]}

Sensse, Maximilian ^{[1
]}

Jones, Peter G. ^{[2
]}

Werz, Daniel B. ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany

[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan & Analyt Chem, Hagenring 30, D-38106 Braunschweig, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 45期

基金：

欧洲研究理事会;

关键词：

bicyclic systems; cycloaddition; cyclopropanes; donor-acceptor compounds; thiocarbonyls; C-H FUNCTIONALIZATION; CATALYTIC ASYMMETRIC DEAROMATIZATION; ARYL IODIDES; PALLADIUM/NORBORNENE CATALYSIS; INTRAMOLECULAR DEAROMATIZATION; AROMATIC FUNCTIONALIZATION; ALLYLIC DEAROMATIZATION; REGIOSPECIFIC SYNTHESIS; SEQUENTIAL REACTIONS; EFFICIENT SYNTHESIS;

D O I：

10.1002/anie.201708346

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lewis-acid-catalyzed reactions of 2-substituted cyclopropane 1,1-dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur-bridged [n.2.1] bicyclic ring systems. Conversion of selenoketones, the heavier analogues, under similar conditions resulted in the formation of various tetrahydroselenophenes.

引用

页码：14293 / 14296

页数：4

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