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A General Approach to Various Five‐ and Six‐Membered gem ‐Difluoroheterocycles: Application to the Synthesis of Fluorinated Analogues of Sedamine
Author(s) -
Hariss Layal,
Ibrahim Rima,
Jaber Nada,
Roisnel Thierry,
Grée René,
Hachem Ali
Publication year - 2018
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.201800371
Subject(s) - heteroatom , intramolecular force , tandem , isomerization , chemistry , base (topology) , combinatorial chemistry , stereochemistry , organic chemistry , ring (chemistry) , catalysis , materials science , mathematics , mathematical analysis , composite material
A new synthesis of a group of O ‐, S ‐ and N ‐heterocycles with a gem ‐difluoro group in position β to the heteroatom has been developed, starting from easily accessible gem ‐difluoro propargylic derivatives. This tandem process involves a base‐induced isomerization followed by an intramolecular 1,4 hetero‐Michael addition. This methodology is suitable for the preparation of five‐ and six‐membered heterocycles and it has been successfully applied to the synthesis of the 3,3‐difluoro analogues of (±)‐sedamine III, (±)‐allosedamine V, (±)‐norallosedamine II, and (±)‐norsedamine IV.