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. 2016 Jan 18;22(3):890-5.
doi: 10.1002/chem.201503823. Epub 2015 Dec 14.

Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds

Masato Senoo  1 , Ayana Furukawa  1 , Takeshi Hata  1   2 , Hirokazu Urabe  3
Affiliations

Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds

Masato Senoo et al. Chemistry. .

Abstract

On treatment of triazoles having an N-sulfonyl-protected benzylamine moiety with [Rh2 (C7 H15 CO2 )4 ], intramolecular C-H bond insertion takes place at the benzylic position to give cis-N-sulfonyl-2-aryl-3-[(sulfonylimino)methyl]pyrrolidines in good yields and with highly stereoselectivities. Analogously, the similar treatment of triazoles having an ether or even an alkyl moiety affords 2-alkyl- or 2-aryl-3-[(sulfonylimino)methyl]tetrahydrofurans or a 2-alkyl-3-[(sulfonylimino)methyl]cyclopentane in good yields.

Keywords: C−H activation; cyclization; heterocycles; rhodium; stereoselectivity.

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