A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources

A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources

We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselective synthesis of spiro-pyrrolidines. Mechanis...

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Veröffentlicht in:Journal of the American Chemical Society 2019-08, Vol.141 (32), p.12536-12540
Hauptverfasser: Lee, Sumin, Lei, Honghui, Rovis, Tomislav
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Aziridines - chemical synthesis
Catalysis
Cycloaddition Reaction
Models, Chemical
Pyrrolidines - chemical synthesis
Rhodium - chemistry
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Zusammenfassung:We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselective synthesis of spiro-pyrrolidines. Mechanistic investigation suggests a Rh­(III)-catalyzed intermolecular aziridination of the alkene and subsequent acid-promoted ring expansion for the pyrrolidine formation.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b07012