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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



Simple Chiral Diene Ligands Provide High Enantioselectivities in Transition-Metal-Catalyzed Conjugate Addition Reactions

K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett., 2008, 10, 4387-4389.

High Performance of a Chiral Diene-Rhodium Catalyst for the Asymmetric 1,4-Addition of Arylboroxines to α,β-Unsaturated Ketones

F.-X. Chen, A. Kina, T. Hayashi, Org. Lett., 2006, 8, 341-344.


Key Words

1,4-Addition, Arylation


ID: J48-Y2003-1580