title: Carbonylation of propargyl carbamates with palladium(II) bisoxazoline catalysts: efficient synthesis of 5-methoxy-3(2H)-furanones.
abstract: Palladium and CO: Carbonylation of 1 with [Pd(tfa)2(±)-L1] (tfa = trifluoroacetate) affords the spirofuranone 2 with inversion of the stereochemistry at C17 in 96 % yield. C17-epi-1 also gave the same product 2 with retention of the stereochemistry at C17. Labelling studies show that (13)CO was incorporated into the C5' position of the furanone ring. The first asymmetric version of this new reaction was achieved.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
authors.forename: Taichi
authors.initials: T
authors.lastname: Kusakabe
authors.forename: Takeo
authors.initials: T
authors.lastname: Takahashi
authors.forename: Rong
authors.initials: R
authors.lastname: Shen
authors.forename: Ayumi
authors.initials: A
authors.lastname: Ikeda
authors.forename: Yogesh Daulat
authors.initials: YD
authors.lastname: Dhage
authors.forename: Yuichro
authors.initials: Y
authors.lastname: Kanno
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Inouye
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Sasai
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Mochida
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kato
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D002219:Carbamates; D005663:Furans; D010080:Oxazoles; D010165:Palladium; D002248:Carbon Monoxide
keywords: alkynes; carbonylation; heterocyles; palladium; synthetic methods