Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis
Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF2 unit in gem‐difluorinated c...
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Published in | Angewandte Chemie International Edition Vol. 63; no. 11; pp. e202319647 - n/a |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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WEINHEIM
Wiley
11.03.2024
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Edition | International ed. in English |
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Abstract | Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF2 unit in gem‐difluorinated cyclopropanes with O−H and C−H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring‐opening process to produce fully‐substituted and configuration‐defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual‐functional copper catalysis, which is involved in both the functionalization of the CF2 unit and the subsequent ring‐opening process.
The synthesis of highly‐substituted alkyl vinyl ethers in a well‐defined configuration is challenging. Now, a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) enabled by dual‐functional Cu catalysis is reported. It also represents a novel ring‐opening pattern involving the cleavage of the C1−C3 bond in gem‐difluorinated cyclopropanes. |
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AbstractList | Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF2 unit in gem‐difluorinated cyclopropanes with O−H and C−H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring‐opening process to produce fully‐substituted and configuration‐defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual‐functional copper catalysis, which is involved in both the functionalization of the CF2 unit and the subsequent ring‐opening process.
The synthesis of highly‐substituted alkyl vinyl ethers in a well‐defined configuration is challenging. Now, a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) enabled by dual‐functional Cu catalysis is reported. It also represents a novel ring‐opening pattern involving the cleavage of the C1−C3 bond in gem‐difluorinated cyclopropanes. Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF2 unit in gem‐difluorinated cyclopropanes with O−H and C−H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring‐opening process to produce fully‐substituted and configuration‐defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual‐functional copper catalysis, which is involved in both the functionalization of the CF2 unit and the subsequent ring‐opening process. Here we present a modular, chemo-, regio-, and stereoselective synthesis of fully-substituted and configuration-defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo- and regioselective functionalization of the CF unit in gem-difluorinated cyclopropanes with O-H and C-H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring-opening process to produce fully-substituted and configuration-defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual-functional copper catalysis, which is involved in both the functionalization of the CF unit and the subsequent ring-opening process. Here we present a modular, chemo-, regio-, and stereoselective synthesis of fully-substituted and configuration-defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo- and regioselective functionalization of the CF2 unit in gem-difluorinated cyclopropanes with O-H and C-H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring-opening process to produce fully-substituted and configuration-defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual-functional copper catalysis, which is involved in both the functionalization of the CF2 unit and the subsequent ring-opening process. Abstract Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple chemical feedstocks. The distinctive approach involves the chemo‐ and regioselective functionalization of the CF 2 unit in gem ‐difluorinated cyclopropanes with O−H and C−H nucleophiles in a specific order. The resulting highly functionalized cyclopropanyl ethers then undergo a stereoselective ring‐opening process to produce fully‐substituted and configuration‐defined AVEs. These AVEs are rarely accessible through conventional methods and are easily transformable. Mechanistic experiments indicate that the success of this method relies on the use of dual‐functional copper catalysis, which is involved in both the functionalization of the CF 2 unit and the subsequent ring‐opening process. |
Author | Chen, Zhengzhao Xia, Ying Jiang, Zhong‐Tao |
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Keywords | Alkyl Vinyl Ethers C-C Bond Activation ACID STEREOSELECTIVE ENTRY YNOL ETHERS Copper Catalysis C-F Bond Functionalization gem-Difluorinated Cyclopropanes C−F Bond Functionalization C−C Bond Activation |
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Snippet | Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs) using simple... Here we present a modular, chemo-, regio-, and stereoselective synthesis of fully-substituted and configuration-defined alkyl vinyl ethers (AVEs) using simple... Abstract Here we present a modular, chemo‐, regio‐, and stereoselective synthesis of fully‐substituted and configuration‐defined alkyl vinyl ethers (AVEs)... |
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SubjectTerms | Alkyl Vinyl Ethers Catalysis Chemistry Chemistry, Multidisciplinary Configurations Copper Copper Catalysis Cyclopropane C−C Bond Activation C−F Bond Functionalization Ethers gem-Difluorinated Cyclopropanes Nucleophiles Organic compounds Physical Sciences Science & Technology Stereoselectivity Substitutes Synthesis Vinyl ethers |
Title | Modular Synthesis of Fully‐Substituted and Configuration‐Defined Alkyl Vinyl Ethers Enabled by Dual‐Functional Copper Catalysis |
URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202319647 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=001147431300001 https://www.ncbi.nlm.nih.gov/pubmed/38198183 https://www.proquest.com/docview/2934038248/abstract/ |
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