3 years ago

Access to Hexahydrocarbazoles: The Thorpe–Ingold Effects of the Ligand on Enantioselectivity

Access to Hexahydrocarbazoles: The Thorpe–Ingold Effects of the Ligand on Enantioselectivity
Liu-Peng Zhao, Lijia Wang, Yong Tang, Hao Chen, Pan Wang, Feng Wang
A novel cyclization reaction of methylenemalonate with indoles is reported, and it provides efficient access to a variety of hexahydrocarbazoles. The enantioselective version was realized by a finely tuned ligand/CuII catalyst. The optically active hexahydrocarbazoles contain three quaternary carbon centers and are obtained in up to 99 % yield with greater than 99:1 d.r. and up to greater than 99 % ee. This reaction can be carried out on gram scale and stereoselective transformation of the product led to the core structure of a series of alkaloids from Kopsia plants. Wing it: By using a newly designed Wing-BOX/CuII catalyst, a cyclization reaction furnished optically active hexahydrocarbazoles, having three quaternary carbon centers and two carbon stereocenters, in up to 99 % yield with greater than 99:1 d.r. and up to greater than 99 % ee.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700042

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