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Synfacts 2010(7): 0805-0805  
DOI: 10.1055/s-0029-1220078
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Acid-Catalyzed Stevens Sigmatropic Rearrangement of N-Allylhydrazones

Contributor(s): Mark Lautens, Jane Panteleev
D. A. Mundal, C. T. Avetta, R. J. Thomson*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

The construction of C-C bonds through sigmatropic rearrangements can be a useful and a non-obvious strategy in synthesis. In this work, the authors explore the acid-catalyzed Stevens [3,3]-sigmatropic rearrangement. The ­described transformation proceeds with moderate to good yields. A variety of E-alkenes are generated in diastereoselectivity of up to 20:1.

Review: For a review on Stevens rearrangement, see: R. V. Stevens, E. E. McEntire, W. E. Barnett, E. Wenkert Chem. Commun. 1973, 662-663.