85048-56-2Relevant academic research and scientific papers
Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones
Engel, Douglas A.,Lopez, Susana S.,Dudley, Gregory B.
, p. 6988 - 6996 (2008/09/21)
In principle, the most efficient and atom-economical means of converting an aldehyde or ketone into the homologated α,β-unsaturated ester is through addition/rearrangement sequences involving acetylenic π-bonds (Scheme 1). Implementation of such a strategy for the synthesis of α,β-unsaturated esters is presented: addition of ethoxyacetylene followed by scandium(III) triflate-catalyzed Meyer-Schuster rearrangement reaction. Stereoselectivities range from good to excellent in the formation of disubstituted α,β-unsaturated esters from aldehydes (Table 3). The two-stage olefination of even the most hindered ketones proceeds with near perfect efficiency (Table 4).
