Enones as Latent Enolates in Catalytic Processes: Catalytic Cycloreduction, Cycloaddition and Cycloisomerization

Ryan R. Huddleston; Michael J. Krische

doi:10.1055/s-2003-36213

ACCOUNT

Enones as Latent Enolates in Catalytic Processes: Catalytic Cycloreduction, Cycloaddition and Cycloisomerization

Ryan R. Huddleston, Michael J. Krische*
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712
e-Mail: mkrische@mail.utexas.edu;

Abstract

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Abstract

The development of catalytic processes predicated on the use of enones as latent enolates circumvents the utilization of chemically labile enol derivatives while enabling regioselective enolate formation. In this account, an overview of this emerging area of catalytic synthetic methodology is presented with an emphasis on intramolecular processes.

1 Introduction: Enones as Latent Enolates
2 Catalytic Hydrometallative Methods
2.1 Reductive Aldol Processes
2.2 Reductive Michael Processes
2.3 Related Catalytic Processes
3 Enones as Homo-Enolates
3.1 Homo-Aldol Cycloreduction
3.2 [2+2]Cycloaddition
4 Nucleophilic Organocatalytic Methods
4.1 Aldol Cycloisomerization (Intramolecular Baylis-Hillman Reaction)
4.2 Michael Cycloisomerization (Intramolecular Rauhut-
Currier Reaction)
5 Outlook

Key words

enones - latent enolates - aldol - Michael reaction - cycloaddition - cycloisomerization

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Referenzen

References

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