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Synthesis of 3‐Methylidene‐2,3‐dihydropyrroles via Formal 1,2‐Enamine Migration/Cyclization Cascade of Rhodium Carbenes.

Authors :
Jie, Yuchen
Hu, Huiqin
Xu, Ze‐Feng
Duan, Shengguo
Li, Chuan‐Ying
Source :
Advanced Synthesis & Catalysis; 1/24/2023, Vol. 365 Issue 2, p161-166, 6p
Publication Year :
2023

Abstract

3‐Methylidene‐2,3‐dihydropyrroles with an ester or keto group at the C4 position were obtained in moderate to good yields from enamine‐tethered triazoles in the presence of a rhodium(II) catalyst. A formal 1,2‐enamine migration/cyclization cascade triggered by formation of an α‐amino carbene is proposed to illustrate the mechanism. The valuable exocyclic double bond showed distinctive reactivity, which is very useful for further introduction of functional groups. The dihydropyrrole is stable under neutral, weakly acidic, or weakly basic conditions. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
16154150
Volume :
365
Issue :
2
Database :
Complementary Index
Journal :
Advanced Synthesis & Catalysis
Publication Type :
Academic Journal
Accession number :
161473463
Full Text :
https://doi.org/10.1002/adsc.202201187