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-Addition

2003/08/27 by Tamio Hayashi, Kazuhito Ueyama, Norihito Tokunaga +1 · 2 citations
Chemistry · #Asymmetric Hydrogenation and Catalysis #Asymmetric Synthesis and Catalysis #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja037367z

openalex publication_date 2003/08/27 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/07

Abstract

As a new type of chiral ligand, a C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene (1) was prepared and used for the rhodium-catalyzed asymmetric addition of organoboron and -tin reagents to alpha,beta-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.

Citations

• Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium Intermediates

Cited by

• Chlorobis(ethylene)rhodium(I) Dimer
• Diene [wikipedia]