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Synthesis of S‐Trifluoromethyl S‐Arylsulfoximine Thioglycosides through Pd‐Catalyzed Migita Cross‐Coupling
Author(s) -
Bennai Nedjwa,
Ibrahim Nada,
Marrot Jérôme,
Belkadi Mohamed,
Alami Mouad,
Magnier Emmanuel,
Anselmi Elsa,
Messaoudi Samir
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.202000821
Subject(s) - trifluoromethyl , chemistry , diastereomer , catalysis , coupling reaction , crystallization , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , alkyl
A general protocol for the synthesis of S‐trifluoromethyl S‐arylsulfoximine thioglycosides has been reported. This protocol is based on a Pd‐catalyzed Migita cross‐coupling between o ‐iodo S‐trifluoromethyl S‐arylsulfoximines and a broad range of 1‐thiosugars. This method gives access to a series of functionalized S‐trifluoromethyl S‐arylsulfoximine thioglycosides in moderate to good yields. Moreover, both diastereoisomers were easily separated by simple crystallization or by HPLC and full characterizations are provided for each pure trifluoromethylsulfoximine.