Stereoselective Formation of Seven-Membered Rings

T. Hashimoto; Y. Naganawa; K. Maruoka

doi:10.1055/s-0029-1217277

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Synfacts 2009(7): 0758-0758
DOI: 10.1055/s-0029-1217277

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Stereoselective Formation of Seven-Membered Rings

Contributor(s): Mark Lautens, David A. Candito
T. Hashimoto, Y. Naganawa, K. Maruoka*
Kyoto University, Japan

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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The authors report a highly diastereoselective Tiffeneau-Demjanov-type ring expansion for the formation of cycloheptanones possessing an all-carbon quaternary stereocenter. Using a chiral auxiliary approach the transformation could be carried out asymmetrically with control of remote stereocenters.