Rhodium‐Catalyzed Intramolecular C−H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds | Zendy

Senoo Masato | Zendy; Furukawa Ayana | Zendy; Hata Takeshi | Zendy; Urabe Hirokazu | Zendy

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

Author(s) -

Senoo Masato,

Furukawa Ayana,

Hata Takeshi,

Urabe Hirokazu

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201503823

Subject(s) - cyclopentane , chemistry , intramolecular force , moiety , alkyl , aryl , sulfonyl , medicinal chemistry , benzylamine , rhodium , ether , catalysis , stereochemistry , organic chemistry

On treatment of triazoles having an N ‐sulfonyl‐protected benzylamine moiety with [Rh 2 (C 7 H 15 CO 2 ) 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.

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