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Synfacts 2011(3): 0301-0301  
DOI: 10.1055/s-0030-1259479
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Promoted Carbometalation of Bicyclic Alkenes

Contributor(s): Mark Lautens, Jane Panteleev
S. Ito, T. Itoh, M. Nakamura*
Kyoto University, Japan
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Publication History

Publication Date:
16 February 2011 (online)

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Significance

The authors describe a diastereoselective arylation of oxa- and azabicyclic alkenes using iron catalysis. Unlike most of the available desymmetrizations of these strained alkenes (see Review below), the method is selective for arylation without ring opening. After carbometalation, the ensuing alkyl iron intermediate could be trapped with a number of electrophiles, such as iodine, allylbromide and acetylchloride, leading to disubstituted products.

Review: M. Lautens, K. Fagnou, S. Hiebert Acc. Chem. Res. 2003, 36, 48-58.