Hydrovinylation of Norbornene. Ligand-Dependent Selectivity and Asymmetric Variations
- 18 October 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (23), 4345-4348
- https://doi.org/10.1021/ol0356284
Abstract
Norbornene undergoes Ni-catalyzed (1−2 mol% allylnickel bromide/phosphine/NaBARF or AgSbF6, 1 bar ethylene, −50 °C) hydrovinylation (>97% yield), giving either a 1:1 or a 2:1 (norbornene/ethylene) adduct depending on the size of the phosphine. Use of binaphthol-derived phosphoramidite ligand results in up to 80% ee for the 1:1 adduct. The course of the reaction is highly dependent on the ligand (size and configuration of the appendages) and the counteranion present.Keywords
This publication has 15 references indexed in Scilit:
- Heterodimerization of Olefins. 1. Hydrovinylation Reactions of Olefins That Are Amenable to Asymmetric CatalysisThe Journal of Organic Chemistry, 2003
- Asymmetric Hydrovinylation ReactionChemical Reviews, 2003
- Hydrovinylation of Alkenes Catalyzed by the Ruthenium−Hydride Complex Formed in Situ from (PCy3)2(CO)RuHCl and HBF4·OEt2Organometallics, 2001
- Synergistic Effects of Hemilabile Coordination and Counterions in Homogeneous Catalysis: New Tunable Monophosphine Ligands for Hydrovinylation ReactionsJournal of the American Chemical Society, 1999
- Hydrovinylation and Related Reactions: New Protocols and Control Elements in Search of Greater Synthetic Efficiency and SelectivityChemistry – A European Journal, 1999
- The Hydrovinylation Reaction: A New Highly Selective Protocol Amenable to Asymmetric CatalysisJournal of the American Chemical Society, 1998
- Synthetic and mechanistic aspects of palladium-catalyzed asymmetric hydrocyanation of alkenes. Crystal structure and reactions of (.eta.2-ethene)(diop)palladiumOrganometallics, 1988
- Kinetic resolution of racemic Grignard reagents by nickel-catalyzed asymmetric Grignard cross-couplingTetrahedron Letters, 1981
- Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysisChemical Reviews, 1977
- Asymmetric Syntheses with the Aid of Homogeneous Transition Metal CatalystsAngewandte Chemie-International Edition, 1973