title: Diastereoselective construction of syn-1,3-dioxanes via a bismuth-mediated two-component hemiacetal/oxa-conjugate addition reaction.
abstract: The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of δ-trialkylsilyloxy and δ-hydroxy α,β-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.
authors.affiliation: Department of Chemistry, The University of Liverpool, Crown Street, Liverpool L69 7ZD, United Kingdom. Andrew.Evans@liverpool.ac.uk
authors.forename: P Andrew
authors.initials: PA
authors.lastname: Evans
authors.forename: Aleksandr
authors.initials: A
authors.lastname: Grisin
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Lawler
mesh_terms: D000080:Acetals / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D001729:Bismuth / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D004146:Dioxanes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000080:Acetals; D000447:Aldehydes; D004146:Dioxanes; D007659:Ketones; D010100:Oxygen; D001729:Bismuth