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Synfacts 2008(7): 0711-0711  
DOI: 10.1055/s-2008-1078455
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Domino Asymmetric Michael Addition/Ylide Epoxidation

Contributor(s): Mark Lautens, Praew Thansandote
Q.-G. Wang, X.-M. Deng, B.-H. Zhu, L.-W. Ye, X.-L. Sun, C.-Y. Li, C.-Y. Zhu, Q. Shen, Y. Tang*
Shanghai Institute of Organic Chemistry and Suzhou University, P. R. of China
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Publikationsdatum:
20. Juni 2008 (online)

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Significance

A domino Michael addition/sulfur ylide epoxidation has been developed to furnish highly substituted cyclohexadiene epoxides. The reaction can occur inter- or intramolecularly and an asymmetric version is shown using two camphor sulfonium salts. The cyclohexadiene epoxides can be further elaborated to give epoxide ring-opening products in a regioselective manner.