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; Kazuhiro Yoshida

doi:10.1021/ja037367z

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

J Am Chem Soc. 2003 Sep 24;125(38):11508-9. doi: 10.1021/ja037367z.

Authors

Tamio Hayashi¹, Kazuhito Ueyama, Norihito Tokunaga, Kazuhiro Yoshida

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. thayashi@kuchem.kyoto-u.ac.jp

PMID: 13129348
DOI: 10.1021/ja037367z

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.