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Synfacts 2006(12): 1251-1251
DOI: 10.1055/s-2006-949499
DOI: 10.1055/s-2006-949499
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Allylic Alkylation with Azlactones Using Triphenylarsine
M. Kawatsura*, D. Ikeda, T. Ishii, Y. Komatsu, J. Uenishi
Tottori University, and Kyoto Pharmaceutical University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200612/lookinside/thumbnails/10.1055-s-2006-949499-1.jpg)
Significance
Allylic alkylation remains an important method for accessing important synthetic intermediates. The authors utilize chiral starting allylic esters and alkylated them with azlactones. Interestingly, the diastereoselectivity was reversed when they switched from bidentate ligands to monodentate ligands. Toluene and NaHMDS was determined to be the best solvent/base system with the bidentate ligands whereas THF and LiHMDS was used with the monodentate ligands. Importantly, this method provides contiguous quaternary-tertiary chiral carbon centers stereoselectively.