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

Kazuhiro Okamoto, Tamio Hayashi* and Viresh H. Rawal*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: thayashikuchem.kyoto-u.ac.jp

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

DOI: 10.1021/ol801931v

Abstract

A chiral diene possessing the bicyclo[2.2.2]octadiene framework substituted with a tertiary alcohol on one of the two double bonds is readily prepared in two steps and is highly effective as a chiral ligand for rhodium-catalyzed asymmetric conjugate addition reactions, giving the corresponding addition products with high enantioselectivity.

see article for more examples

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

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

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

T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc., 2003, 125, 11508-11509.

Tuning the Chiral Environment of C2-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes

R. Shintani, Y. Ichikawa, K. Takatsu, F.-X. Chen, T. Hayashi, J. Org. Chem., 2009, 74, 869-873.

Key Words

1,4-additions, 1,4-addition of arenes

ID: J54-Y2008-2820