Lewis base-catalyzed additions of alkynes using trialkoxysilylalkynes.
[reaction: see text]. The Lewis base-catalyzed additions of alkynyl nucleophiles to aldehydes, ketones, and imines is described. Mechanistic studies strongly indicate that the use of new triethoxysilylalkynes facilitates access of a reactive hypervalent silicate intermediate. This activated carbon nucleophile subsequently undergoes rapid addition to carbonyl compounds and imines, thus affording the secondary and tertiary propargyl systems in moderate to high yield.
Lettan Ii
Robert B
RB
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Scheidt
Karl A
KA