Simple Chiral Diene Ligands Provide High Enantioselectivities in Transition-Metal-Catalyzed Conjugate Addition Reactions
- 5 September 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (19) , 4387-4389
Abstract
Chiral dienes possessing the bicyclo[2.2.2]octadiene framework were prepared readily through the [4 + 2] cycloaddition of (R)-α-phellandrene with methyl propiolate as the key step. Diene 9, substituted with a tertiary alcohol on one of the two double bonds, is prepared in just one step from the cycloadduct and is highly effective as a chiral ligand for rhodium-catalyzed asymmetric conjugate addition reactions, giving the corresponding addition products with higher enantioselectivity than other chiral dienes.Keywords
This publication has 43 references indexed in Scilit:
- Chiral Olefins as Steering Ligands in Asymmetric CatalysisAngewandte Chemie International Edition, 2008
- More than Bystanders: The Effect of Olefins on Transition‐Metal‐Catalyzed Cross‐Coupling ReactionsAngewandte Chemie International Edition, 2008
- Some new C2-symmetric bicyclo[2.2.1]heptadiene ligands: synthesis and catalytic activity in rhodium(I)-catalyzed asymmetric 1,4- and 1,2-additionsTetrahedron, 2007
- Expanding the C2-Symmetric Bicyclo[2.2.1]hepta-2,5-diene Ligand Family: Concise Synthesis and Catalytic Activity in Rhodium-Catalyzed Asymmetric AdditionThe Journal of Organic Chemistry, 2006
- Carbon−Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition ReactionOrganic Letters, 2005
- Highly Chemo‐ and Enantioselective Arylative Cyclization of Alkyne‐Tethered Electron‐Deficient Olefins Catalyzed by Rhodium Complexes with Chiral DienesAngewandte Chemie International Edition, 2005
- Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amidesChemical Communications, 2005
- Preparation of C2-Symmetric Bicyclo[2.2.2]octa-2,5-diene Ligands and Their Use for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic AcidsThe Journal of Organic Chemistry, 2005
- C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-TosylaryliminesJournal of the American Chemical Society, 2004
- A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts: Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-AdditionJournal of the American Chemical Society, 2003