Synfacts 2011(6): 0648-0648  
DOI: 10.1055/s-0030-1260393
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of γ-Quaternary Acylcyclopentenes via a Ring-Contraction Strategy

Contributor(s): Mark Lautens, Patrick T. Franke
A. Y. Hong, M. R. Krout, T. Jensen, N. B. Bennett, A. M. Harned, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
Further Information

Publication History

Publication Date:
19 May 2011 (online)

Significance

The authors describe a catalytic enantioselective allylation-ring-contraction sequence for the synthesis of densely functionalized chiral acylcyclopentenes. The palladium-catalyzed asymmetric alkylation affords precursors in excellent yields and high enantioselectivities. The subsequent mild ring contraction via a retro aldol-­aldol sequence affords important chiral building blocks.