Asymmetric Intramolecular Arylcyanation of Unactivated Olefins via C-CN Bond Activation

Mary P. Watson and Eric N. Jacobsen*

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, Email: jacobsenchemistry.harvard.edu

M. P. Watson, E. N. Jacobsen, J. Am. Chem. Soc., 2008, 130, 12594-12595.

DOI: 10.1021/ja805094j

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Abstract

A highly enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni(0) catalyst, BPh₃ as co-catalyst, and TangPHOS as a chiral ligand. Two new C-C bonds and one quaternary carbon stereogenic center are generated in a single synthetic step, converting readily available benzonitriles into 1,1-disubstituted indanes in good yield.

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Key Words

indanes

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ID: J48-Y2008-2560