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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-?-allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

SUBMITTER: Yang S

PROVIDER: S-EPMC5994874 | biostudies-other | 2018 Jun

REPOSITORIES: biostudies-other

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

Yang Song S Li Quan-Zhe QZ Xu Chen C Xu Qin Q Shi Min M

Chemical science 20180511 22

We reported a highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes <i>via</i> 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 t ...[more]

PMID: 29938038

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