Palladium-Catalyzed γ-Selective and Stereospecific Allyl−Aryl Coupling between Allylic Acetates and Arylboronic Acids

Allyl−aryl coupling between allylic acetates and arylboronic acids took place in the presence of catalytic amounts of Pd(OAc)2, 1,10-phenanthroline, and AgSbF6 with high γ-selectivity and E/Z-selectivity. The reaction of an optically active allylic acetates with an α-stereogenic center proceeded wit...

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Veröffentlicht in:Journal of the American Chemical Society 2008-12, Vol.130 (51), p.17276-17277
Hauptverfasser: Ohmiya, Hirohisa, Makida, Yusuke, Tanaka, Tatsunori, Sawamura, Masaya
Format: Artikel
Sprache:eng
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Zusammenfassung:Allyl−aryl coupling between allylic acetates and arylboronic acids took place in the presence of catalytic amounts of Pd(OAc)2, 1,10-phenanthroline, and AgSbF6 with high γ-selectivity and E/Z-selectivity. The reaction of an optically active allylic acetates with an α-stereogenic center proceeded with excellent α-to-γ chirality transfer with syn-selectivity and gave the corresponding optically active allyl−aryl coupling products with a stereogenic center at the benzylic position.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja808673n