title: Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: highly efficient synthesis of enantiopure (-)-erythrodiene.
abstract: Easily prepared allyl phenyl sulfones, capable of introduction of the alkene by electrophilic alpha-substitution, are superior to allyl acetates as substrates for Pd-catalyzed Zn-ene cyclizations, providing C5 or C(4)N rings with cis-1,2-vinyl and -CH(2)Zn substituents. Several examples, with different methods of substrate preparation, are presented. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Kai
authors.initials: K
authors.lastname: Deng
authors.forename: Justin
authors.initials: J
authors.lastname: Chalker
authors.forename: Ao
authors.initials: A
authors.lastname: Yang
authors.forename: Theodore
authors.initials: T
authors.lastname: Cohen
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry
chemical_list: D000498:Allyl Compounds; D013141:Spiro Compounds; D013450:Sulfones; C511223:erythrodiene; D010165:Palladium; D015032:Zinc