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Synfacts 2006(7): 0686-0686
DOI: 10.1055/s-2006-941815
DOI: 10.1055/s-2006-941815
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Development of a New ‘Axially Chiral’ Bisphosphine Ligand
R. Shintani, K. Yashio, T. Nakamura, K. Okamoto, T. Shimada, T. Hayashi*
Kyoto University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Juni 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200607/lookinside/thumbnails/10.1055-s-2006-941815-1.jpg)
Significance
The authors describe the synthesis of a new axially chiral bisphosphine ligand, which is shown to be extremely effective for the isomerization of racemic α-arylpropargyl alcohols to yield β-chiral indanones. The newly designed ligand outperformed all of the ‘standard’ bisphosphine ligands, including BINAP, MeO-biphep, segphos and H8-BINAP. The authors subjected enantioenriched α-arylpropargyl alcohols to the reaction conditions and found that only the S-enantiomer reacted! They concluded that the initial formation of the ketone is the subject of kinetic resolution.