Enantiopure 2‐(Trifluoromethyl)‐1,2,3,4‐tetrahydronaphthalene‐1,2‐diols from a Tartaric Acid Derived Scaffold | Zendy

Massicot Fabien | Zendy; nenmacher Jean | Zendy; Grellepois Fabienne | Zendy; Portella Charles | Zendy

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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.

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