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Synfacts 2011(3): 0301-0301
DOI: 10.1055/s-0030-1259479
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
S. Ito, T. Itoh, M. Nakamura*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
16 February 2011 (online)
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.