A Mild and Efficient Method for the Stereoselective Formation of C−O Bonds: Palladium-Catalyzed Allylic Etherification Using Zinc(II) Alkoxides
- 1 November 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (24) , 4369-4371
- https://doi.org/10.1021/ol027104u
Abstract
[reaction: see text] A highly chemo- and stereoselective palladium-catalyzed allylic etherification reaction is described. The use of zinc(II) alkoxides proved effective in promoting the addition of the oxygen nucleophile derived from aliphatic alcohols to eta(3)-allylpalladium complexes. Using diethylzinc (0.5 equiv), 5 mol % of Pd(OAc)(2), and 7.5 mol % of 2-di(tert-butyl)phosphinobiphenyl in THF, the cross-coupling reaction between various aliphatic alcohols and allylic acetates proceeded at ambient temperature to furnish allylic ethers with high stereoselectivity.Keywords
This publication has 21 references indexed in Scilit:
- The bioinorganic chemistry of zinc: synthetic analogues of zinc enzymes that feature tripodal ligandsChemical Communications, 2000
- Asymmetric Carbon–Carbon Bond‐Forming Reactions: Asymmetric Allylic Alkylation ReactionsPublished by Wiley ,2000
- Rhodium-Catalyzed Asymmetric Alcoholysis and Aminolysis of Oxabenzonorbornadiene: A New Enantioselective Carbon−Heteroatom Bond Forming ProcessJournal of the American Chemical Society, 2000
- Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl EthersJournal of the American Chemical Society, 1999
- Diastereoselective Synthesis of Vinylmorpholines by Palladium-Catalyzed Tandem Allylic Substitutions using Enantiopure Aminoalcohols as Bifunctional NucleophilesTetrahedron Letters, 1995
- Organotin nucleophiles. 6. Palladium-catalyzed allylic etherification with tin alkoxidesThe Journal of Organic Chemistry, 1985
- Alkoxides as nucleophiles in (.pi.-allyl)palladium chemistry. Synthetic and mechanistic studiesJournal of the American Chemical Society, 1983
- 2-Substituted tetrahydrofurans of known absolute stereochemistry by ScN' chirality transferJournal of the American Chemical Society, 1983
- Allylic alkylation. Palladium-catalyzed substitutions of allylic carboxylates. Stereo- and regiochemistryJournal of the American Chemical Society, 1980
- Methods of formation of the ether linkagePublished by Wiley ,1967