title: Pd(II)-SDP-catalyzed enantioselective 5-exo-dig cyclization of γ-alkynoic acids: application to the synthesis of functionalized dihydofuran-2(3H)-ones containing a chiral quaternary carbon center.
abstract: The Pd(II)-SDP-catalyzed first enantioselective intramolecular cyclization of α,α-disubstituted γ-alkynoic acids is described. This 5-exo-dig cyclization afforded dihydrofuran-2(3H)-ones bearing a chiral quaternary carbon center in excellent yields with enantioselectivities up to 71%. A mechanism involving palladium(II) species is proposed to rationalize the outcome of the reaction.
authors.affiliation: The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. sasai@sanken.osaka-u.ac.jp.
authors.forename: Vellaisamy
authors.initials: V
authors.lastname: Sridharan
authors.forename: Lulu
authors.initials: L
authors.lastname: Fan
authors.forename: Shinobu
authors.initials: S
authors.lastname: Takizawa
authors.forename: Takeyuki
authors.initials: T
authors.lastname: Suzuki
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Sasai
mesh_terms: D000143:Acids / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000143:Acids; D000480:Alkynes; D001688:Biological Products; D005663:Furans; D010165:Palladium