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. 2003 Sep 24;125(38):11508-9.
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

Tamio Hayashi  1 , Kazuhito Ueyama, Norihito Tokunaga, Kazuhiro Yoshida
Affiliations

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 et al. J Am Chem Soc. .

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.

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