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
收藏
页码：6250 / 6253
页数：4
相关论文
共 113 条
[41]   Donor-acceptor cyclopropanes as three-carbon components in a [4+3] cycloaddition reaction with 1,3-diphenylisobenzofuran [J].
Ivanova, Olga A. ;
Budynina, Ekaterina M. ;
Grishin, Yuri K. ;
Trushkov, Igor V. ;
Verteletskii, Pavel V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1107-1110
[42]   Lewis Acid Triggered Vinylcyclopropane-Cyclopentene Rearrangement [J].
Ivanova, Olga A. ;
Chagarovskiy, Alexey O. ;
Shumsky, Alexey N. ;
Krasnobrov, Vasiliy D. ;
Leyina, Irina I. ;
Trushkov, Igor V. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02) :543-560
[43]   Lewis Acid Catalyzed Selective Reactions of Donor-Acceptor Cyclopropanes with 2-Naphthols [J].
Kaicharla, Trinadh ;
Roy, Tony ;
Thangaraj, Manikandan ;
Gonnade, Rajesh G. ;
Biju, Akkattu T. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (34) :10061-10064
[44]   Rearrangements of Furan-, Thiophene- and N-Boc-Pyrrole-Derived Donor-Acceptor Cyclopropanes: Scope and Limitations [J].
Kaschel, Johannes ;
Schneider, Tobias F. ;
Schirmer, Patrick ;
Maass, Christian ;
Stalke, Dietmar ;
Werz, Daniel B. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (21) :4539-4551
[45]   Symmetric and unsymmetric 3,3′-linked bispyrroles via ring-enlargement reactions of furan-derived donor-acceptor cyclopropanes [J].
Kaschel, Johannes ;
Schneider, Tobias F. ;
Kratzert, Daniel ;
Stalke, Dietmar ;
Werz, Daniel B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (21) :3494-3509
[46]   Donor-acceptor cyclopropanes with Lawesson's and Woollins' reagents: formation of bisthiophenes and unprecedented cage-like molecules [J].
Kaschel, Johannes ;
Schmidt, Christian D. ;
Mumby, Mark ;
Kratzert, Daniel ;
Stalke, Dietmar ;
Werz, Daniel B. .
CHEMICAL COMMUNICATIONS, 2013, 49 (39) :4403-4405
[47]   Domino Reactions of Donor-Acceptor-Substituted Cyclopropanes for the Synthesis of 3,3′-Linked Oligopyrroles and Pyrrolo[3,2-e]indoles [J].
Kaschel, Johannes ;
Schneider, Tobias F. ;
Kratzert, Daniel ;
Stalke, Dietmar ;
Werz, Daniel B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (44) :11153-11156
[48]   Friedel-Crafts-Type Reactions with Electrochemically Generated Electrophiles from Donor-Acceptor Cyclopropanes and -Butanes [J].
Kolb, Simon ;
Ahlburg, Nils L. ;
Werz, Daniel B. .
ORGANIC LETTERS, 2021, 23 (14) :5549-5553
[49]   Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity [J].
Kreft, Alexander ;
Luecht, Alexander ;
Grunenberg, Joerg ;
Jones, Peter G. ;
Werz, Daniel B. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) :1955-1959
[50]   The Cyclopropyl Group as a Neglected Donor in Donor-Acceptor Cyclopropane Chemistry [J].
Kreft, Alexander ;
Jones, Peter G. ;
Werz, Daniel B. .
ORGANIC LETTERS, 2018, 20 (07) :2059-2062
12345678910