Allylic Etherification via Ir(I)/Zn(II) Bimetallic Catalysis
- 1 June 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (13) , 2679-2682
- https://doi.org/10.1021/ol0508328
Abstract
[reaction: see text] An efficient allylic etherification of aliphatic alcohols with allylic carbonates has been achieved by an iridium catalysis using stoichiometric zinc alkoxides or a two-component bimetallic catalytic system where the Ir(I) catalyst acts on allylic carbonates to generate electrophiles while aliphatic alcohols are separately activated by Zn(II) coordination to function as nucleophilies. This reaction occurs with complete regiospecificity and tolerates a wide range of functional groups.Keywords
This publication has 25 references indexed in Scilit:
- Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium‐Catalyzed Allylic Etherification: Total Synthesis of Gaur AcidAngewandte Chemie International Edition in English, 2004
- Iridium‐Catalyzed Intermolecular Allylic Etherification with Aliphatic Alkoxides: Asymmetric Synthesis of Dihydropyrans and DihydrofuransAngewandte Chemie International Edition in English, 2004
- Stereoselective Palladium-Catalyzed O-Glycosylation Using GlycalsJournal of the American Chemical Society, 2004
- Catalytic Enone Cycloallylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal CatalysisJournal of the American Chemical Society, 2003
- The bioinorganic chemistry of zinc: synthetic analogues of zinc enzymes that feature tripodal ligandsChemical Communications, 2000
- A Two-Component Catalyst System for Asymmetric Allylic Alkylations with Alcohol PronucleophilesJournal of the American Chemical Society, 1998
- Iridium Complex-Catalyzed Allylic Alkylation of Allylic Esters and Allylic Alcohols: Unique Regio- and StereoselectivityJournal of the American Chemical Society, 1998
- Conservation of Absolute Configuration in the Acyclic Rhodium-Catalyzed Allylic Alkylation Reaction: Evidence for an Enyl (σ + π) Organorhodium IntermediateJournal of the American Chemical Society, 1998
- Highly Selective Allylic Alkylation with a Carbon Nucleophile at the More Substituted Allylic Terminus Catalyzed by an Iridium Complex: An Efficient Method for Constructing Quaternary Carbon CentersAngewandte Chemie International Edition in English, 1997
- An Enantioselective Two-Component Catalyst System: Rh−Pd-Catalyzed Allylic Alkylation of Activated NitrilesJournal of the American Chemical Society, 1996