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Synlett 2017; 28(04): 415-424
DOI: 10.1055/s-0036-1588109
DOI: 10.1055/s-0036-1588109
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All-Carbon (4+2) Annulations Catalysed by N-Heterocyclic Carbenes
Weitere Informationen
Publikationsverlauf
Received: 12. Oktober 2016
Accepted after revision: 07. November 2016
Publikationsdatum:
16. Dezember 2016 (online)
Abstract
Less than five years ago we reported the NHC-catalysed (4+2) annulation of dienol ethers and unsaturated acyl fluorides. From a mechanistic perspective, this reaction likely involves a vinylogous Michael addition followed by an aldol/β-lactonisation cascade. In this account, the discovery of this reaction and ensuing studies into its mechanism and utility in multistep synthesis will be examined. The subsequent development of chiral catalysts designed for this reaction and the achievement of a first-generation and later second-generation approach to an enantioselective variant of this reaction will be discussed. Finally, related redox isomerisation cascades leading to benzaldehydes will be introduced, as will reactions in the field of NHC catalysis that exploit similar reaction cascades.
1 Introduction
2 Reaction Design and Discovery
3 Mechanistic Studies and β-Lactone Interception
4 Enantioselective Cyclohexenyl β-Lactone Synthesis
5 Enantioselective Cyclohexadiene Synthesis
6 Redox Isomerisation
7 Related NHC Catalysis
8 Conclusions
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For reactions that likely involve Brønsted base chemistry see:
For NHC catalyzed transesterification with amino alcohols and mechanistic comments see:
For Lewis base addition to ahydrides see:
For Lewis base addition to enol carbonates see:
For selected examples from the Chi group with ester substrates see:
For a recent example from the Xu group see:
For in situ anhydride formation and reaction see:
For a selection of recent reviews of NHC catalysis see:
For selected reviews of dienamine catalysis see:
For all-carbon (4+2) annulations through vinylogous Michael aldol-type cascades see:
For NHC-catalyzed reactions involving β-lactones see:
For a useful review on 2-pyrones and 2-pyridones in synthesis see:
For recent examples in catalysis see:
For enzymatic versions see:
For selected studies in total synthesis see:
For methodologies see: