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Catalytic Intramolecular C(sp 3 )–H Amination of Carbamimidates
Author(s) -
Grelier Gwendal,
ReyRodriguez Romain,
Darses Benjamin,
Retailleau Pascal,
Dauban Philippe
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700263
Subject(s) - amination , intramolecular force , catalysis , chemistry , allylic rearrangement , medicinal chemistry , nitrogen , stereochemistry , organic chemistry
The Rh II ‐catalyzed intramolecular C(sp 3 )–H amination of carbamimidates allowed new nitrogen heterocycles to be isolated in yields up to 99 %. The reaction was best performed in the presence of the Rh 2 (esp) 2 (esp = α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionic acid) complex by using 2,2,2‐trichloroethoxysulfonyl‐protected compounds. The reaction could be applied to substrates possessing a benzylic, an allylic, a propargylic, or a tertiary C(sp 3 )–H bond.