A Novel Example of Chiral Counteranion Induced Enantioselective Metal Catalysis: The Importance of Ion-Pairing in Copper-Catalyzed Olefin Aziridination and Cyclopropanation
- 1 December 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (26), 4165-4168
- https://doi.org/10.1021/ol000303y
Abstract
A new ion-pairing route to achieve asymmetric catalysis has been observed in the copper-catalyzed aziridination of styrene with a chiral counteranion. Structural studies suggest that enantioinduction occurs via ion-pairing of the cationic copper catalyst in the chiral pocket created by the anion. The degree of asymmetric induction can be tuned with features that affect ion-pairing, such as achiral and chiral ligands, temperature, and solvent polarity.Keywords
This publication has 6 references indexed in Scilit:
- Asymmetric Synthesis of an Organic Compound with High Enantiomeric Excess Induced by Inorganic Ionic Sodium ChlorateAngewandte Chemie-International Edition, 2000
- Diastereoselective Ion Pairing of TRISPHAT Anions and Tris(4,4′-dimethyl-2,2′-bipyridine)iron(II)Angewandte Chemie-International Edition, 1998
- Studies on Catalytic Asymmetric Imine Hydrogenation in the Presence of Reverse Micelles: Enhanced Enantioselectivity due to Surfactant Head Group CoordinationOrganometallics, 1996
- Designed catalyst for enantioselective Diels-Alder addition from a C2-symmetric chiral bis(oxazoline)-iron(III) complexJournal of the American Chemical Society, 1991
- A Borate Propeller Compound as Chiral Catalyst for an Asymmetrically Induced Diels‐Alder ReactionAngewandte Chemie-International Edition, 1990
- Electron spin resonance spectra and structures of 9-benzonorbornenyl and 9-benzonorbornadienyl radicalsJournal of the American Chemical Society, 1975