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Nucleophilic Rh I Catalyzed Selective Isomerization of Terminal Aziridines to Enamides
Author(s) -
Tian Yingying,
Kunz Doris
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000597
Subject(s) - isomerization , catalysis , chemistry , nucleophile , rhodium , styrene , nucleophilic addition , lewis acids and bases , double bond , medicinal chemistry , aziridine , terminal (telecommunication) , conjugated system , photochemistry , organic chemistry , copolymer , polymer , ring (chemistry) , telecommunications , computer science
The selective isomerization of various terminal N ‐Boc protected aziridines to enamides was realized using the highly reactive nucleophilic rhodium catalyst C with the Lewis acid LiNTf 2 as co‐catalyst under moderate conditions. The reaction proceeds smoothly with only 1 mol% catalyst loading and excellent yields were achieved. An intermediate containing an enamide with a non‐conjugated terminal C=C double bond was detected during the course of the reaction, which isomerizes to form the thermodynamically favored 2‐amido styrene. Mechanistic insight is gained based on these observations.