Regio- and Stereoselective Synthesis of Alkyl Allylic Ethers via Gold(I)-Catalyzed Intermolecular Hydroalkoxylation of Allenes with Alcohols
- 16 April 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (10) , 2079-2081
- https://doi.org/10.1021/ol800646h
Abstract
Reaction of 1-phenyl-1,2-butadiene with 2-phenyl-1-ethanol catalyzed by a 1:1 mixture of a gold(I) N-heterocyclic carbene complex and AgOTf at room temperature for 1 h led to isolation of (E)-(3-phenethoxy-1-butenyl)benzene in 96% yield as a single regio- and stereoisomer. Gold(I)-catalyzed intermolecular allene hydroalkoxylation was effective for monosubsituted, 1,1- and 1,3-disubstituted, trisubstituted, and tetrasubstituted allenes and for a range of primary and secondary alcohols, methanol, phenol, and propionic acid.Keywords
This publication has 33 references indexed in Scilit:
- A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal CatalysisScience, 2007
- Allylic Etherification via Ir(I)/Zn(II) Bimetallic CatalysisOrganic Letters, 2005
- 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
- Stereoselective Palladium-Catalyzed O-Glycosylation Using GlycalsJournal of the American Chemical Society, 2004
- Halide ion effects in the rhodium-catalyzed allylic substitution reaction using copper(I) alkoxides and enolatesTetrahedron: Asymmetry, 2003
- A Mild and Efficient Method for the Stereoselective Formation of C−O Bonds: Palladium-Catalyzed Allylic Etherification Using Zinc(II) AlkoxidesOrganic Letters, 2002
- Regio- and Enantiospecific Rhodium-Catalyzed Allylic Etherification Reactions Using Copper(I) Alkoxides: Influence of the Copper Halide Salt on SelectivityJournal of the American Chemical Society, 2002
- A Two-Component Catalyst System for Asymmetric Allylic Alkylations with Alcohol PronucleophilesJournal of the American Chemical Society, 1998
- Synthetic Routes to Allenic Acids and Esters and Their Stereospecific Conversion to ButenolidesThe Journal of Organic Chemistry, 1997
- Synthesis of 2,5-Dihydrofurans and 5,6-Dihydro-2H-pyrans by Silver(I)-Catalyzed Cyclization of Allenic AlcoholsSynthesis, 1979