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

被引：12
|
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
收藏
页码：6250 / 6253
页数：4
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