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. 2009;42(3):55-66.

Discovering New Reactions with N-Heterocyclic Carbene Catalysis

Eric M Phillips  1 , Audrey Chan, Karl A Scheidt
Affiliations

Discovering New Reactions with N-Heterocyclic Carbene Catalysis

Eric M Phillips et al. Aldrichimica Acta. 2009.
No abstract available

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Figures

Figure 1
Figure 1
Proposed Stabilization of N-Heterocyclic Carbenes through σ and π Electronic Effects. (Ref. 22)
Scheme 1
Scheme 1
Asymmetric Benzoin Condensation.
Scheme 2
Scheme 2
Single-Flask Furan and Pyrrole Synthesis by the Conjugate Addition of Acylsilanes to α,β-Unsaturated Ketones. (Ref. 37,38)
Scheme 3
Scheme 3
Hydroacylation of α-Keto Esters and 1,2-Diketones. (Ref. 44)
Scheme 4
Scheme 4
Oxidation of Inactivated Aldehydes to the Corresponding Esters via a Benzylic-Type Alcohol Intermediate. (Ref. 46)
Scheme 5
Scheme 5
Envisaged Generation of Vinylogous Carbonyl Anions (Homoenolates). (Ref. 49)
Scheme 6
Scheme 6
Proposed Pathway for β Protonation. (Ref. 49,52)
Scheme 7
Scheme 7
NHC-Catalyzed β Protonation. (Ref. 49,52)
Scheme 8
Scheme 8
Formal [3 + 3] Cycloadditions with Homoenolates.
Scheme 9
Scheme 9
Homoenolate Additions to Nitrones and Elaboration of the Resulting Products into γ-Amino Esters. (Ref. 70)
Scheme 10
Scheme 10
Proposed Pathway for Enolate Formation and Three-Atom Functionalization. (Ref. 77)
Scheme 11
Scheme 11
Application of the NHC-Catalyzed Desymmetrization to the Synthesis of Bakkenolides I, J, and S. (Ref. 79b)
Scheme 12
Scheme 12
Proposed Pathway for the NHC-Catalyzed Mannich Reaction of A-Aryloxy Aldehydes. (86b)
Scheme 13
Scheme 13
Investigation of Trapping Reagents for the Mannich-Type Reaction of A-Aryloxy Aldehydes. (Ref. 86b)
Figure 2
Figure 2
New Concepts in Carbene Catalysis.
Figure 3
Figure 3
Milestones in the Growth of This Area of Organocatalysis over the Past Five Years.
See this image and copyright information in PMC

References

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