Chiral Norbornadienes as Efficient Ligands for the Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Fumaric and Maleic Compounds

Chiral Norbornadienes as Efficient Ligands for the Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Fumaric and Maleic Compounds

A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in th...

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Veröffentlicht in:Organic letters 2004-09, Vol.6 (19), p.3425-3427
Hauptverfasser: Shintani, Ryo, Ueyama, Kazuhito, Yamada, Ichiro, Hayashi, Tamio
Format: Artikel
Sprache:eng
Schlagworte:
Boronic Acids - chemistry
Catalysis
Fumarates - chemical synthesis
Ligands
Maleates - chemical synthesis
Molecular Structure
Norbornanes - chemistry
Rhodium - chemistry
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Zusammenfassung:A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048421z