Synfacts 2007(8): 0829-0829  
DOI: 10.1055/s-2007-968773
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cycloheptane-1,4-diones by an Asymmetric Ring-Expanding Allylation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. R. Schulz, S. Blechert*
Technische Universität Berlin, Germany
Further Information

Publication History

Publication Date:
24 July 2007 (online)

Significance

The authors describe the synthesis of chiral seven-membered carbocycles via a ring-expansion-allylation sequence under palladium catalysis. A variety of cycloheptane 1,4-diones are obtained with quaternary stereocenters with moderate to high enantioselectivity. The syntheses of similar compounds with tertiary stereocenters proceed with much lower stereoselectivity.