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Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles

Michael J. James, Rosa E. Clubley, Kleopas Y. Palate, Thomas J. Procter, Anthony C. Wyton, Peter O'Brien, Richard J. K. Taylor* and William P. Unsworth*

*Department of Chemistry, University of York, Heslington, York, YO10 5DD, U.K., Email: richard.tayloryork.ac.uk, william.unsworthyork.ac.uk

M. J. James, R. E. Clubley, K. Y. Palate, T. J. Procter, A. C. Wyton, P. O'Brien, R. J. K. Taylor, W. P. Unsworth, Org. Lett., 2015, 17, 4372-4375.

DOI: 10.1021/acs.orglett.5b02216


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Abstract

Either spirocyclic indolenines or carbazoles can be generated from a common indole-tethered propargyl alcohol precursor in high yields upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford ()-actinopolymorphol B is also reported.

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Key Words

carbazoles


ID: J54-Y2015