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

Sumin Lee | Zendy; Honghui Lei | Zendy; Tomislav Rovis | Zendy

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

Author(s) -

Sumin Lee,

Honghui Lei,

Tomislav Rovis

Publication year - 2019

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b07012

Subject(s) - chemistry , nitrene , pyrrolidine , alkene , catalysis , intermolecular force , ring (chemistry) , terminal (telecommunication) , formal synthesis , combinatorial chemistry , organic chemistry , medicinal chemistry , molecule , telecommunications , computer science

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.

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