Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi

doi:10.1039/C8SC01595C

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes†

Song Yang,^a Quan-Zhe Li,^a Chen Xu,^a Qin Xu^a and Min Shi

*^abc

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* Corresponding authors

^a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
E-mail: mshi@sioc.ac.cn

^b State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P. R. China

^c State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

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.

This article is part of the themed collection: Celebrating 100 Years of Chemistry at Nankai University

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DOI: https://doi.org/10.1039/C8SC01595C
Article type: Edge Article
Submitted: 08 اپریل 2018
Accepted: 09 میٔ 2018
First published: 11 میٔ 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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

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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.

Chemical Science

Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes†

Abstract

Supplementary files

Article information

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Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes

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