title: Diastereoselective construction of anti-4,5-disubstituted-1,3-dioxolanes via a bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde.
abstract: The bismuth-mediated two-component hemiacetal oxa-conjugate addition of γ-hydroxy-α,β-unsaturated ketones with paraformaldehyde affords anti-4,5-disubstituted-1,3-dioxolanes in an efficient and stereoselective manner. The reaction provides a practical, inexpensive and atom-economical approach to these types of heterocycles, which represent useful intermediates for target-directed synthesis and precursors to syn-1,2-diols.
authors.affiliation: Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, ON K7L 3N6, Canada. Andrew.Evans@chem.queensu.ca.
authors.forename: Aleksandr
authors.initials: A
authors.lastname: Grisin
authors.forename: Samuel
authors.initials: S
authors.lastname: Oliver
authors.forename: Michael D
authors.initials: MD
authors.lastname: Ganton
authors.forename: John
authors.initials: J
authors.lastname: Bacsa
authors.forename: P Andrew
authors.initials: PA
authors.lastname: Evans
mesh_terms: D001729:Bismuth / Q000737:chemistry*; D004148:Dioxolanes / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004148:Dioxolanes; D007659:Ketones; D011108:Polymers; D005557:Formaldehyde; D001729:Bismuth; C003043:paraform