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Synfacts 2009(1): 0065-0065  
DOI: 10.1055/s-0028-1087436
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Asymmetric Allyic Alkylation of Unstabilized Nucleophiles

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
B. M. Trost*, D. A. Thaisrivongs
Stanford University, USA
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

This paper describes the first highly enantioselective palladium-catalyzed asymmetric allylic alkylation (AAA) with unstabilized ”hard" ­nucleophiles. The complexation of the ”hard" ­nucleophile with BF3 makes the nucleophile soft, which allowed the authors to use this ”hard" nucleophile in AAA reactions. Furthermore, the resulting product could be applied to diastereoselective dihydroxylation as well as epoxidation.