Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Arylmethylene Cyanoacetates
- 25 January 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (4) , 589-592
Abstract
Asymmetric 1,4-addition of arylboronic acids to (E)-methyl 2-cyano-3-arylpropenoates proceeded in the presence of a rhodium catalyst (3 mol %) coordinated with a chiral diene ligand, (R,R)-Ph-bod*, to give high yields of the corresponding methyl 3,3-diaryl-2-cyanopropanoates with high enantioselectivity (up to 99% ee). This catalytic asymmetric transformation was applied to the asymmetric synthesis of (R)-tolterodine.Keywords
This publication has 39 references indexed in Scilit:
- 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[3.3.1]nonadiene as a Chiral Ligand for Rhodium-Catalyzed Asymmetric Arylation of N-(4-Nitrobenzenesulfonyl)aryliminesOrganic Letters, 2004
- Catalytic Asymmetric Arylative Cyclization of Alkynals: Phosphine-Free Rhodium/Diene Complexes as Efficient CatalystsJournal of the American Chemical Society, 2004
- 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
- Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to EnonesJournal of the American Chemical Society, 1998
- Rhodium-Catalyzed Conjugate Addition of Aryl- or 1-Alkenylboronic Acids to EnonesOrganometallics, 1997