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Synthesis of Enantiopure α ‐Alkoxy‐ α ‐Trifluoromethyl Aldehydes and Carboxylic Acids from Trifluoromethyl Ketones
Author(s) -
Fernández Rosario,
MartínZamora Eloísa,
Pareja Carmen,
Vázquez Juan,
Díez Elena,
Monge Angeles,
Lassaletta José M.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981231)37:24<3428::aid-anie3428>3.0.co;2-p
Subject(s) - trifluoromethyl , chemistry , enantiopure drug , synthon , moiety , hydrazone , adduct , alkoxy group , organic chemistry , carboxylic acid , formaldehyde , ketone , medicinal chemistry , enantioselective synthesis , catalysis , alkyl
Formaldehyde dialkylhydrazones behave as neutral d 1 synthons in their uncatalyzed reaction with trifluoromethyl ketones (see reaction). Both racemic and optically pure 1,2‐adducts were obtained in good yields. Efficient deprotection of the hydrazone moiety afforded interesting fluorinated quaternary compounds such as 1 and 2 .