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, Email: thayashikuchem.kyoto-u.ac.jp
T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc., 2003, 125, 11508-11509.
DOI: 10.1021/ja037367z
Abstract
The C2-symmetric norbornadiene derivative (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene was used as ligand for the rhodium-catalyzed asymmetric 1,4-addition of organoboron and -tin reagents to α,β-unsaturated ketones, which gave high yields of the addition products with up to 99% enantioselectivity.
see article for more reactions
K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett., 2008, 10, 4387-4389.
F.-X. Chen, A. Kina, T. Hayashi, Org. Lett., 2006, 8, 341-344.
Key Words
ID: J48-Y2003-1580