title: A continuous homologation of esters: an efficient telescoped reduction-olefination sequence.
abstract: A continuous protocol for the two-carbon homologation of esters to α,β-unsaturated esters is described. This multireactor homologation telescopes an ester reduction, phosphonate deprotonation, and Horner-Wadsworth-Emmons olefination, thus converting a three-operation procedure into a single, uninterrupted system that eliminates the need for isolation or purification of the aldehyde intermediates. The homologated products are obtained in high yield and selectivity.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Damien
authors.initials: D
authors.lastname: Webb
authors.forename: Timothy F
authors.initials: TF
authors.lastname: Jamison
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004952:Esters; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004952:Esters; D063065:Organophosphonates