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Synfacts 2009(2): 0163-0163
DOI: 10.1055/s-0028-1087569
DOI: 10.1055/s-0028-1087569
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Desymmetrization of Diallyl Acetals of Alkynals by Rodium Catalysis
D. E. Kim, B. H. Lee, M. Rajagopalasarma, J.-P. Genêt, V. Ratovelomanana-Vidal*, N. Jeong*
Korea University, Seoul, Korea and Ecole Nationale Supérieure de Chimie de Paris, France
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Januar 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200902/lookinside/thumbnails/10.1055-s-0028-1087569-1.jpg)
Significance
The rodium/chiral phosphine catalyzed Pauson-Khand reaction is applied to the desymmetrization of diallyl acetals of alkynals to afford a diastereomeric mixture of cyclopentenone products which, after hydrolysis, provide single diastereomers with high enantiomeric excess. Ligand effects are discussed in detail, and the solvent - cinnamaldehyde - is used as a convenient source of carbon monoxide.