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DOI: 10.1055/s-0036-1589470
Enantioselective Cascade Reactions under N-Heterocyclic Carbene Catalysis
Publication History
Received: 09 July 2016
Accepted after revision: 28 July 2016
Publication Date:
30 November 2016 (online)

Abstract
The use of chiral N-heterocyclic carbenes (NHCs) as catalysts in asymmetric synthesis has opened a wide range of applications due to their unique ability to generate reaction intermediates with unusual reactivity patterns that very often involve the reversal of the typical polarity associated with the functional groups present in the starting materials. In this sense, the direct activation of aldehydes or surrogates by these reactive species provides different chemical structures (conjugated Breslow intermediates, azolium enolates and dienolates, or unsaturated acyl azolium cations) which constitute excellent platforms for initiating cascade or domino reactions in the presence of a polyfunctional reagent.
1 Introduction
2 Cascade Reactions Initiated by the Participation of Homoenolate Equivalents
3 Cascade Reactions Initiated by the Participation of Azolium Enolates
4 Cascade Reactions Initiated by the Participation of Dienolate Equivalents
5 Cascade Reactions Initiated by the Participation of α,β-Unsaturated Acyl Azolium Intermediates
6 Summary and Outlook
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For selected reviews covering the concept of biomimetic synthesis, see:
For a recent review in benzoin condensations, see:
For selected reviews in NHC catalysis, see:
See also:
Review on NHC-catalyzed domino reactions:
For general reviews on cascade or domino reactions:
Pioneering reports in non-stereoselective versions:
See also:
See also:
For a previous non-stereoselective version, see:
For a mechanistic computational study, see:
For a related example, see:
For the use of β-bromoenals as alkynal equivalents in this reaction, see:
See also:
See also:
See also:
For a related example, see:
Pioneering report (achiral version):
Enantioselective version:
See also:
See also:
See also:
For related examples, see:
For another example of related [4+2]-type reactivity, see:
For a pioneering report, see:
For related [4+2] annulations using isatins as electrophiles, see:
The same reaction can also be carried out using α-bromoenals as starting materials:
For a related reaction using trifluoromethyl ketones as electrophiles, see:
For related examples, see:
For other related examples, see:
See also:
See also:
For a related version using N-hydroxybenzotriazolyl esters, see: