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Z-Selective Copper-Catalyzed Asymmetric Allylic Alkylation with Grignard Reagents

Massimo Giannerini, Martín Fañanás-Mastral and Ben L. Feringa*

*Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands, Email:

M. Giannerini, M. Fañanás-Mastral, B. L. Feringa, J. Am. Chem. Soc., 2012, 134, 4108-4111.

DOI: 10.1021/ja300743t

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Allylic gem-dichlorides undergo regio- and enanantioselective copper-catalyzed allylic alkylation with Grignard reagents to afford chiral Z-vinyl chlorides. Subsequent Suzuki cross coupling reactions afford optically active Z-alkenes and 1,3-cis,trans dienes.

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Key Words

Allylation, Vinyl chlorides

ID: J48-Y2012-0660