title: Preparation and use of enantioenriched allenylsilanes for the stereoselective synthesis of homopropargylic ethers.
abstract: A convenient procedure for the synthesis of highly enantioenriched allenylsilanes by Johnson orthoester Claisen rearrangement of 1-silyl propargylic alcohols is described. Allenylsilanes are then used as carbon nucleophiles in three-component, Lewis acid mediated additions to in situ generated oxonium ions, resulting in enantioenriched homopropargylic ethers.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, MA 02215, USA.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Brawn
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D007202:Indicators and Reagents; D012821:Silanes; D012997:Solvents; D010293:Pargyline; D008049:Lipase