title: Stereoselective organozinc addition reactions to 1,2-dihydropyrans for the assembly of complex pyran structures.
abstract: [reaction: see text] Nucleophilic addition of organozincs to 1,2-dihydropyranyl acetates represents a new, broadly defined method for the stereocontrolled synthesis of alpha-substituted pyrans. The products obtained from this process are versatile materials that can be used to construct C-glycosides and other functionalized pyran structures of import. The occurrence of pyranyl groups in both natural products and therapeutically active agents confers added value to the studies described herein.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305, USA.
authors.forename: Dietrich P
authors.initials: DP
authors.lastname: Steinhuebel
authors.forename: James J
authors.initials: JJ
authors.lastname: Fleming
authors.forename: J
authors.initials: J
authors.lastname: Du Bois
mesh_terms: D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D009942:Organometallic Compounds; D011714:Pyrans; D015032:Zinc