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Enantiopure 2‐(Trifluoromethyl)‐1,2,3,4‐tetrahydronaphthalene‐1,2‐diols from a Tartaric Acid Derived Scaffold
Author(s) -
Massicot Fabien,
nenmacher Jean,
Grellepois Fabienne,
Portella Charles
Publication year - 2010
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.200901153
Subject(s) - enantiopure drug , chemistry , trifluoromethylation , trifluoromethyl , tartaric acid , nucleophile , intramolecular force , amide , organic chemistry , hydrolysis , stereochemistry , enantioselective synthesis , medicinal chemistry , catalysis , alkyl , citric acid
The synthesis of the four stereoisomers of 2‐(trifluoromethyl)tetrahydronaphthalene‐1,2‐diols and/or their 2‐ O ‐allyl derivatives is reported. Nucleophilic trifluoromethylation of a tartaric acid derived keto amide, and a one‐pot hydrolysis/oxidative cleavage/intramolecular Friedel–Crafts transformation are the main features of this synthesis.