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Synfacts 2008(4): 0384-0384  
DOI: 10.1055/s-2008-1042794
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Tandem C-C and C-Cl Bond Formations

Contributor(s): Mark Lautens, Praew Thansandote
D. A. Mundal, J. J. Lee, R. J. Thomson*
Northwestern University, Evanston, USA
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Publikationsdatum:
19. März 2008 (online)

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Significance

Based on the Stevens rearrangement (R. V. Stevens et al. J. Chem. Soc., Chem. Commun. 1973, 662), the authors have disclosed a new Cu(II)-mediated [3,3]-sigmatropic rearrangement of N-allylhydrazones. Essentially, a C-C and a C-Cl bond are formed in a tandem reaction. The scope is broad for a variety of substrates and includes regio- and stereoselective examples.