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Synfacts 2008(1): 0083-0083  
DOI: 10.1055/s-2007-991447
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Allylic Substitution with Retention of Regio- and Stereoinformation

Contributor(s): Paul Knochel, Tobias Thaler
Y. Yatsumonji, Y. Ishida, A. Tsubouchi, T. Takeda*
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

This protocol presents a regio- and stereoselective method for nickel-catalyzed allylic substitutions. Hereby, the inexpensive and air-stable Ni[P(OEt)3]4 was employed and sodium sulfides, alcoholates and phenolates were used as nucleophiles. The reaction generally proceeds with good to excellent yields and the stereoinformation of the double-bond is retained.