Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes

被引：13

作者：

Mloston, Grzegorz ^{[1
]}

Kowalczyk, Mateusz ^{[1
]}

Augustin, Andre U. ^{[2
]}

Jones, Peter G. ^{[3
]}

Werz, Daniel B. ^{[2
]}

机构：

[1] Univ Lodz, Dept Organ & Appl Chem, Tamka 12, PL-91403 Lodz, Poland

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

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 46期

基金：

欧洲研究理事会;

关键词：

Cycloaddition; D-A cyclopropanes; Lewis acids; Sulfur heterocycles; Thioketenes; SUBSTITUTED CYCLOPROPANES; CYCLOADDITION REACTIONS; 3-COMPONENT REACTION; HETARYL THIOKETONES; EFFICIENT SYNTHESIS; RING-ENLARGEMENT; NITRILE IMINES; 3+2 ANNULATION; PHENYL AZIDE; CONSTRUCTION;

D O I：

10.1002/ejoc.202100879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactivity of donor-acceptor (D-A) cyclopropanes towards thioketenes was investigated. In a (3+2)-cycloaddition using Sc(OTf)(3) as a Lewis acidic catalyst, the corresponding exocyclic thioenol ethers (2-methylidene tetrahydrothiophenes) were formed in moderate to good yields. Unsymmetrical thioketenes provided E/Z mixtures at the double bond, with the Z isomer being preferred.

引用

页码：6250 / 6253

页数：4

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