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Synfacts 2009(3): 0302-0302  
DOI: 10.1055/s-0028-1087773
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Protonation of Friedel-Crafts Intermediates

Contributor(s): Hisashi Yamamoto, Pingfan Li
M. P. Sibi*, J. Coulomb, L. M. Stanley
North Dakota State University, Fargo, USA
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

This Zn/Ph-dbbox catalyzed enantioselective Friedel-Crafts reaction is realized through a stereo-defining protonation step of the initial 1,4-addition intermediate. The isoxazolidi­none group is identified as the best chelating group to give ideal reactivity and selectivity.