title: N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.
abstract: Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.
authors.affiliation: Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
authors.forename: Troy E
authors.initials: TE
authors.lastname: Reynolds
authors.forename: Charlotte A
authors.initials: CA
authors.lastname: Stern
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; D012821:Silanes