DOI
doi:10.1016/j.tetlet.2007.03.088
Abstract
A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig’s base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75–97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for full conversion.
Document Type
Post-print Article
Publication Date
5-14-2007
Publisher Statement
Copyright © 2007, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.
DOI: 10.1016/j.tetlet.2007.03.088
Full Citation:
Downey, C. Wade, and Miles W. Johnson. "A Tandem Enol Silane Formation-Mukaiyama Aldol Reaction Mediated by TMSOTf." Tetrahedron Letters 48, no. 20 (May 14, 2007): 3559-562. doi:10.1016/j.tetlet.2007.03.088.
Recommended Citation
Downey, C. Wade and Johnson, Miles W., "A Tandem Enol Silane Formation-Mukaiyama Aldol Reaction Mediated by TMSOTf" (2007). Chemistry Faculty Publications. 11.
https://scholarship.richmond.edu/chemistry-faculty-publications/11