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Synfacts 2006(8): 0817-0817  
DOI: 10.1055/s-2006-941950
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral Cyclopentanones via Asymmetric Ring Expansion

Contributor(s): Mark Lautens, Andrew Martins
B. M. Trost*, J. Xie
Stanford University, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

In the presence of a Pd(0)/Trost ligand system, allenylcyclobutanols are efficiently and enantioselectively converted into chiral cyclopentanones via Pd-π-allyl directed ring expansion. A wide variety of allenyl and cyclobutyl substituents are tolerated, affording cyclopentanone products in good to excellent yields and enantiomeric excesses.