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Synfacts 2006(2): 0155-0155  
DOI: 10.1055/s-2005-924786
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Allylic Amines from Allylic Ethers and Zirconocene Imides

Contributor(s): Paul Knochel, Andrei Gavryushin
G. Lalic, S. Blum, R. G. Bergman*
University of California at Berkeley, USA
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Although many SN2′ reactions with carbon nucleophiles are known, those reactions with heteroatomic nucleophiles have not been explored so well. Here, a new, very promising synthetic transformation is described. It allows the enantioselective preparation of allylic amines from available chiral (Z)-allylic ethers. The synthetic protocol is very easy to perform, and the reaction conditions tolerate many functional groups.