title: Generation of ketenes from acid chlorides using NaH/crown ether shuttle-deprotonation for use in asymmetric catalysis.
abstract: [reaction: see text] We describe methodology for the in situ generation of reactive monosubstituted ketenes from acid chlorides through a shuttle deprotonation process using NaH as an inexpensive stoichiometric base and a crown ether cocatalyst. We have successfully applied this new procedure to the catalytic, asymmetric synthesis of beta-lactams and alpha-haloesters.
authors.affiliation: Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Taggi
authors.forename: Harald
authors.initials: H
authors.lastname: Wack
authors.forename: Ahmed M
authors.initials: AM
authors.lastname: Hafez
authors.forename: Stefan
authors.initials: S
authors.lastname: France
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis; D007769:Lactams / Q000138:chemical synthesis; D011522:Protons
chemical_list: D000475:Alkenes; D002712:Chlorides; D004988:Ethers, Cyclic; D007202:Indicators and Reagents; D007659:Ketones; D007769:Lactams; D011522:Protons