Scope of Palladium-Catalyzed Alkylative Ring Opening
- 16 January 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (5), 1437-1447
- https://doi.org/10.1021/ja037550s
Abstract
We have explored the scope of the palladium-catalyzed nucleophilic ring opening methodology. New highly selective and highly active catalysts have been found for the ring opening of oxabenzonorbornadienes. Employing these catalysts, the addition of various alkyl nucleophiles to oxabenzonorbornadiene has been achieved. In addition, reaction of diethylzinc with [3.2.1] oxabicyclic alkenes has been accomplished to yield ring-opened products as well as functionalized alkene addition products.Keywords
This publication has 27 references indexed in Scilit:
- Palladium-Catalyzed Enantioselective Alkylative Ring OpeningJournal of the American Chemical Society, 2000
- Mechanism of Palladium Complex-Catalyzed Enantioselective Mannich-Type Reaction: Characterization of A Novel Binuclear Palladium Enolate ComplexJournal of the American Chemical Society, 1999
- New Formulas for Organozincate ChemistryJournal of the American Chemical Society, 1998
- Highly Enantioselective Catalytic Conjugate Addition and Tandem Conjugate Addition–Aldol Reactions of Organozinc ReagentsAngewandte Chemie-International Edition, 1997
- Ring Opening in the Hydrostannation of Methylenecyclopropanes: Effect of the Catalyst and SubstrateJournal of the American Chemical Society, 1996
- Unprecedented Intra‐ and Intermolecular Palladium‐Catalyzed Coupling Reactions with Methylenecylclopropane‐Type Tetrasubstituted AlkenesAngewandte Chemie-International Edition, 1995
- Stereoselective Reactions Mediated by Functionalized DiorganozincsSynlett, 1995
- Improved Procedure for the Synthesis of Enantiomerically Enriched Cyclopropylmethanol DerivativesThe Journal of Organic Chemistry, 1995
- Catalytic Enantioselective Conjugate Addition of Dialkylzinc Compounds to ChalconesEuropean Journal of Inorganic Chemistry, 1992
- Ultrasound in organic synthesis. 7. Preparation of organozinc reagents and their nickel-catalyzed reactions with .alpha.,.beta.-unsaturated carbonyl compoundsThe Journal of Organic Chemistry, 1985