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Synthesis of α‐Chlorolactams by Cyanoborohydride‐Mediated Radical Cyclization of Trichloroacetamides
Author(s) -
Coussanes Guilhem,
Jakobi Harald,
Lindell Stephen,
Bonjoch Josep
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800210
Subject(s) - sodium cyanoborohydride , allylic rearrangement , chemistry , radical cyclization , trifluoromethyl , bicyclic molecule , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
A cyanoborohydride‐promoted radical cyclization methodology has been developed to access α‐chlorolactams in a simple and efficient way using NaBH 3 CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of α‐chlorolactams (mono‐ and bicyclic), which were tested for herbicidal activity, trans ‐3‐chloro‐4‐methyl‐1‐(3‐trifluoromethyl)phenyl‐2‐pyrrolidinone being the most active.
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