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Intermolecular [3+2] Cycloaddition of Cyclopropylamines with Olefins by Visible-Light Photocatalysis

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  • We thank the University of Arkansas, the Arkansas Bioscience Institute, and the NIH NCRR COBRE grant (P30 RR031154) for generous support of this research. R.S.S thanks the Division of Organic Chemistry of the ACS for a SURF award. We also thank Prof. Bill Durham for insightful discussions on photochemistry and Prof. Jim Hinton for obtaining NOESY spectra.

Abstract

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It's the power of light! A visible-light-mediated intermolecular [3+2] cycloaddition of mono- and bicyclic cyclopropylamines with olefins catalyzed by [Ru(bpz)3](PF6)2⋅2 H2O has been developed to furnish aminocyclopentane derivatives in good yields (see scheme, bpz=2,2′-bipyrazine). Saturated 5,5- and 6,5-fused heterocycles are obtained in synthetically useful yields and diastereoselectivity.

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