Stereoselective Synthesis of Tetrahydrofurans via the Palladium-Catalyzed Reaction of Aryl Bromides with γ-Hydroxy Alkenes: Evidence for an Unusual Intramolecular Olefin Insertion into a Pd(Ar)(OR) Intermediate
- 23 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (6) , 1620-1621
- https://doi.org/10.1021/ja0394838
Abstract
A new, stereoselective method for the synthesis of substituted tetrahydrofurans from γ-hydroxy alkenes that forms both a C−C and a C−O bond with diastereoselectivities of up to >20:1 is described. Initial mechanistic studies that suggest the reactions proceed via the intramolecular insertion of an olefin into a Pd(Ar)(OR) intermediate are discussed.Keywords
This publication has 8 references indexed in Scilit:
- Palladium Alkoxides: Potential Intermediacy in Catalytic Amination, Reductive Elimination of Ethers, and Catalytic Etheration. Comments on Alcohol Elimination from Ir(III)Journal of the American Chemical Society, 1996
- Synthetic routes to 2,5-disubstituted tetrahydrofuransTetrahedron: Asymmetry, 1993
- Oxygen-atom transfer from nitrous oxide to a nickel metallacycle. Synthesis, structure, and reactions of [cyclic] (2,2'-bipyridine)Ni(OCH2CH2CH2CH2)Journal of the American Chemical Society, 1993
- Controlled molecular aggregation. 1. Cyclic trimerization via hydrogen bondingThe Journal of Organic Chemistry, 1992
- New stragegy for the total synthesis of 1.alpha.-hydroxyvitamin D derivativesJournal of the American Chemical Society, 1992
- Intramolecular alkoxy-carbonylation of hydroxy alkenes promoted by Pd(II)Pure and Applied Chemistry, 1990
- Hydride transfer to transition-metal carbonyls in the gas phase. The heat of formation of (CO)4FeCHO-Organometallics, 1985
- Synthesis and rearrangement of methanesulfonate esters of N-hydroxyacetanilides. A model for a penultimate carcinogenJournal of the American Chemical Society, 1984