N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.
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.
Reynolds
Troy E
TE
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Stern
Charlotte A
CA
Scheidt
Karl A
KA
D000447:Aldehydes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*
D000447:Aldehydes; D006571:Heterocyclic Compounds; D012821:Silanes