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