C1-Symmetric Dicyclopentadienes as New Chiral Diene Ligands for Asymmetric Rhodium-Catalyzed Arylation of N-Tosylarylimines
- 12 August 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (17), 3820-3823
- https://doi.org/10.1021/ol101531r
Abstract
Monosubstituted C1-symmetric dicyclopentadienes as a new class of diene ligands have been developed for asymmetric arylation of N-tosylarylimines in excellent yields (98−99%) with high enantioselectivities (90−96%). The preparation of these diene ligands relied on an efficient lipase-catalyzed resolution as the key step.Keywords
This publication has 51 references indexed in Scilit:
- Small Band Gap Polymers Synthesized via a Modified Nitration of 4,7-Dibromo-2,1,3-benzothiadiazoleOrganic Letters, 2010
- Rhodium‐Catalyzed Asymmetric Conjugate Addition of Organoboronic Acids to Nitroalkenes Using Chiral Bicyclo[3.3.0] Diene LigandsAngewandte Chemie International Edition, 2010
- Chemoenzymatic Synthesis and Application of Bicyclo[2.2.2]octadiene Ligands: Increased Efficiency in Rhodium‐Catalyzed Asymmetric Conjugate Additions by Electronic TuningAngewandte Chemie International Edition, 2010
- Chiral Tetrafluorobenzobarrelene Ligands for the Rhodium‐Catalyzed Asymmetric Cycloisomerization of Oxygen‐ and Nitrogen‐Bridged 1,6‐EnynesAngewandte Chemie International Edition, 2010
- Catalytic Enantioselective Formation of Chiral-Bridged Dienes Which Are Themselves Ligands for Enantioselective CatalysisOrganic Letters, 2009
- Control of Chemo-, Regio-, and Stereoselectivities in Ligand-Free Pd-Catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate with Allyl EstersOrganic Letters, 2009
- Tuning the Chiral Environment of C2-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienesThe Journal of Organic Chemistry, 2008
- Enantiomerically pure bicyclo[3.3.1]nona-2,6-diene as the sole source of enantioselectivity in BIPHEP-Rh asymmetric hydrogenationChemical Communications, 2008
- Simple Chiral Diene Ligands Provide High Enantioselectivities in Transition-Metal-Catalyzed Conjugate Addition ReactionsOrganic Letters, 2008
- Preparation of the Synthetic Equivalents of Chiral Cyclohexadienone and Cycloheptadienone: The Enantio- and Diastereo-controlled Synthesis of (-)-Clavularin BSynlett, 1999