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

Table of Contents
|
Journal Home Page
|
Search the Journals

Full Text HTML
Supporting Info
Download Citation
Purchase Article

J. Am. Chem. Soc., 125 (38), 11508 -11509, 2003. 10.1021/ja037367z S0002-7863(03)07367-0
Web Release Date: August 27, 2003

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

Tamio Hayashi,* Kazuhito Ueyama, Norihito Tokunaga, and Kazuhiro Yoshida

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

thayashi@kuchem.kyoto-u.ac.jp

Received July 18, 2003

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 ,-unsaturated ketones, which gave high yields of the 1,4-addition products with up to 99% enantioselectivity.

Download the full text: PDF | HTML