Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanesElectronic supplementary information (ESI) available: Experimental procedures and characterization data of the new compounds. CCDC 1538522, 1525845, and 1822276. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01595c

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of... 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 TMMRh model complex was proposed, providing an atom economical Rh--allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Science Royal Society of Chemistry

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanesElectronic supplementary information (ESI) available: Experimental procedures and characterization data of the new compounds. CCDC 1538522, 1525845, and 1822276. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01595c

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Publisher
The Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
2041-6520
D.O.I.
10.1039/c8sc01595c
Publisher site
See Article on Publisher Site

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 TMMRh model complex was proposed, providing an atom economical Rh--allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

Journal

Chemical ScienceRoyal Society of Chemistry

Published: May 18, 2018

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