Issue 22, 2018

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

Abstract

We reported a highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes via cationic Rh(I) catalysis in this context. The combination of various secondary amines and indoles with keto-vinylidenecyclopropanes afforded the corresponding hydrofunctionalization products in good to excellent yields with outstanding ee values under mild conditions. A new TMM–Rh model complex was proposed, providing an atom economical Rh-π-allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

Graphical abstract: Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Apr. 2018
Accepted
09 Maijs 2018
First published
11 Maijs 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 5074-5081

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

S. Yang, Q. Li, C. Xu, Q. Xu and M. Shi, Chem. Sci., 2018, 9, 5074 DOI: 10.1039/C8SC01595C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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