A practical method for the synthesis of 2-alkynylpropenals.
A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation. Critical to the success of this approach is the use of a special workup procedure for the oxidation step. The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.
Thongsornkleeb
Charnsak
C
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Danheiser
Rick L
RL
D000171:Acrolein / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry
D014753:Vinyl Compounds; D000171:Acrolein