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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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 57; no. 15; pp. 3862 - 3873
Main Authors: Chen, Xiang‐Yu, Liu, Qiang, Chauhan, Pankaj, Enders, Dieter
Format: Journal Article
Language:English
Published: Germany Wiley Subscription Services, Inc 03.04.2018
Edition:International ed. in English
Subjects:
Asymmetric synthesis
carbenes
Catalysis
Chemical reactions
Chemical synthesis
Cycloaddition
Enantiomers
Intermediates
organocatalysis
reaction mechanisms
organocatalysis
carbenes
reaction mechanisms
asymmetric synthesis
cycloaddition
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary: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.
Bibliography:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201709684