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Stereoselective Synthesis of Dienes from N-Allylhydrazones

Devon A. Mundal, Kelly E. Lutz and Regan J. Thomson*

*Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, Email: r-thomsonnorthwestern.edu

D. A. Mundal, K. E. Lutz, R. J. Thomson, Org. Lett., 2009, 11, 465-468.

DOI: 10.1021/ol802585r (free Supporting Information)


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Abstract

A stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives offers high levels of (E)-stereoselectivity for a variety of substrates. Addition of a dienophile to the reaction mixture allows a one-flask diene synthesis-cycloaddition sequence.

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Key Words

Dienes, NBS


ID: J54-Y2009-0300