Synfacts 2007(10): 1076-1076  
DOI: 10.1055/s-2007-969021
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of β-Lactones

Contributor(s): Mark Lautens, Praew Thansandote
T. Kull, R. Peters*
ETH Zürich, Switzerland
Further Information

Publication History

Publication Date:
07 November 2007 (online)

Significance

An aluminum-catalyzed enantio­selective [2+2] cycloaddition of ketenes and aldehydes provides a practical synthesis of enantio­enriched β-lactones. The Al source is either DIBAL-H or Et3Al and the ligand is either a di­phenyl or a dicyclohexyldiamine. Both α-branched and α-unbranched aldehydes are compatible with the reaction conditions, producing β-lactones in high yields and moderate to good ee values.