title: A practical method for the synthesis of 2-alkynylpropenals.
abstract: 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.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Charnsak
authors.initials: C
authors.lastname: Thongsornkleeb
authors.forename: Rick L
authors.initials: RL
authors.lastname: Danheiser
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D014753:Vinyl Compounds; D000171:Acrolein