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N-Heterocyclic Carbene-Initiated α-Acylvinyl Anion Reactivity: Additions of α-Hydroxypropargylsilanes to Aldehydes

Troy E. Reynolds, Charlotte A. Stern and Karl A. Scheidt*

*Department of Chemistry, Northwestern University, Evanston, Illinois 60208, Email: scheidtnorthwestern.edu

T. E. Reynolds, C. A. Stern, K. A. Scheidt, Org. Lett., 2007, 9, 2581-2584.

DOI: 10.1021/ol0710515 (free Supporting Information)


Abstract

Highly substituted α,β-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of α-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the Morita-Baylis-Hillman reaction.

see article for more examples


proposed mechanism for NHC-initiated pathway



Stereoselective Lewis Acid-Catalyzed α-Acylvinyl Additions

T. E. Reynolds, A. R. Bharadwaj, K. A. Scheidt, J. Am. Chem. Soc., 2006, 128, 15382-15383.


Key Words

Brook Rearrangement, Baylis-Hillman Adducts


ID: J54-Y2007-2030