Synfacts 2009(2): 0163-0163  
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

Contributor(s): Hisashi Yamamoto, Pingfan Li
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
Further Information

Publication History

Publication Date:
22 January 2009 (online)

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.