title: Pd(II)-catalyzed cascade reaction with 1,3-chirality transfer; stereoselective synthesis of chiral nonracemic 2,2'-THF-THF ring units.
abstract: A Pd(II)-catalyzed cascade reaction of chiral nonracemic allylic alcohols possessing an internal mono- or diepoxide and a terminal alcohol provided a contiguous THF-THF ring unit stereospecifically. The cyclization takes place in a 5-exo-tet-5-exo-trig fashion with high chirality transfer through a syn-S(N)2' like process for the formation of the internal THF ring. Chiral bis- and tris-THF-THF ring units were effectively prepared from acyclic precursors by the Pd-catalyzed reaction.
authors: Kyoto Pharmaceutical University, Yamashina, Kyoto, 607-8412, Japan. juenishi@mb.kyoto-phu.ac.jp
authors: Jun'ichi
authors: J
authors: Uenishi
authors: Yuhei
authors: Y
authors: Fujikura
authors: Nobuyuki
authors: N
authors: Kawai
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D005663:Furans; C018674:tetrahydrofuran; D010165:Palladium