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Synthesis of Novel Cyclic Nitrones with gem ‐Difluoroalkyl Side Chains Through Cascade Reactions
Author(s) -
Soulieman Ali,
Ibrahim Rima,
Barakat Zeinab,
Gouault Nicolas,
Roisnel Thierry,
Boustie Joel,
Grée René,
Hachem Ali
Publication year - 2020
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.202000972
Subject(s) - isomerization , domino , chemistry , side chain , bicyclic molecule , molecule , cascade reaction , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , polymer
New five‐membered cyclic nitrones with gem ‐difluoroalkyl groups in γ‐position have been prepared by a 3‐step sequence starting from propargylic alcohols. This domino process involves a base‐mediated isomerization reaction to enones, which are trapped in situ by nitroalkane anions. In a final step, starting from these key precursors, a reduction‐cyclization process affords the target molecules. Mono‐ and bicyclic nitrones have been prepared by this route which allows, as well, the synthesis of nitrones with functional groups in terminal position of the side chain.