N‐Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Remote Enantioselective Functionalizations
N‐heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC‐catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β‐unsaturated acyl azoliums, homoenolate equivalents, and azolium...
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| Published in: | Angewandte Chemie International Edition Vol. 57; no. 15; pp. 3862 - 3873 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Germany
Wiley Subscription Services, Inc
03.04.2018
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| Edition: | International ed. in English |
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| ISSN: | 1433-7851, 1521-3773, 1521-3773 |
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| Abstract | N‐heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC‐catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β‐unsaturated acyl azoliums, homoenolate equivalents, and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in NHC‐catalyzed asymmetric cycloaddition reactions involving azolium dienolate intermediates.
An intermediate look: N‐heterocyclic carbene catalysis has emerged as a powerful strategy for enantioselective functionalizations at remote positions, and proceeds via azolium dienolate intermediates that are easily generated from various substrates. This Minireview highlights the development and the new advances of cycloaddition/annulation reactions involving azolium dienolate intermediates. |
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| AbstractList | N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC-catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β-unsaturated acyl azoliums, homoenolate equivalents, and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in NHC-catalyzed asymmetric cycloaddition reactions involving azolium dienolate intermediates. N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC-catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β-unsaturated acyl azoliums, homoenolate equivalents, and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in NHC-catalyzed asymmetric cycloaddition reactions involving azolium dienolate intermediates.N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC-catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β-unsaturated acyl azoliums, homoenolate equivalents, and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in NHC-catalyzed asymmetric cycloaddition reactions involving azolium dienolate intermediates. N‐heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on NHC‐catalyzed transformations involving Breslow intermediates, acyl azoliums, α,β‐unsaturated acyl azoliums, homoenolate equivalents, and azolium enolates. However, the azolium dienolate intermediates generated by NHCs have been employed in asymmetric synthesis only very recently, especially in cycloadditions dealing with remote functionalization. This Minireview highlights all the developments and the new advances in NHC‐catalyzed asymmetric cycloaddition reactions involving azolium dienolate intermediates. An intermediate look: N‐heterocyclic carbene catalysis has emerged as a powerful strategy for enantioselective functionalizations at remote positions, and proceeds via azolium dienolate intermediates that are easily generated from various substrates. This Minireview highlights the development and the new advances of cycloaddition/annulation reactions involving azolium dienolate intermediates. |
| Author | Enders, Dieter Chen, Xiang‐Yu Liu, Qiang Chauhan, Pankaj |
| Author_xml | – sequence: 1 givenname: Xiang‐Yu surname: Chen fullname: Chen, Xiang‐Yu organization: RWTH Aachen University – sequence: 2 givenname: Qiang surname: Liu fullname: Liu, Qiang organization: RWTH Aachen University – sequence: 3 givenname: Pankaj surname: Chauhan fullname: Chauhan, Pankaj organization: RWTH Aachen University – sequence: 4 givenname: Dieter orcidid: 0000-0001-6956-7222 surname: Enders fullname: Enders, Dieter email: enders@rwth-aachen.de organization: RWTH Aachen University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29136320$$D View this record in MEDLINE/PubMed |
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| Keywords | organocatalysis carbenes reaction mechanisms asymmetric synthesis cycloaddition |
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| Snippet | N‐heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on... N-heterocyclic carbene (NHC) catalysis has emerged as a powerful strategy in organic synthesis. In recent years a number of reviews have been published on... |
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| SubjectTerms | Asymmetric synthesis carbenes Catalysis Chemical reactions Chemical synthesis Cycloaddition Enantiomers Intermediates organocatalysis reaction mechanisms |
| Title | N‐Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Remote Enantioselective Functionalizations |
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