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Fluorination of Hydroxyesters with N,N‐Diethyl‐1,1,2,3,3,3‐Hexafluoro Propaneamine
Author(s) -
Watanabe S.,
Fujita T.,
Sakamoto M.,
Arai T.,
Kttazume T.
Publication year - 1989
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf03022752
Subject(s) - chemistry , lipase , hydrolysis , organic chemistry , medicinal chemistry , stereochemistry , enzyme
Abstract The reactions of N,N‐diethyl‐1,1,2,3,3,3‐hexafluoro propaneamine (PPDA) with Β‐hydroxyl esters gave their corresponding fluorides. For example, methyl (S)‐(+)‐3‐fluorobutyrate was obtained from the reaction of methyl (R)‐(‐)‐3‐hydroxybutyrate with PPDA. The reaction of a ‐hydroxy esters with PPDA gave a mixture of their corresponding fluorides and 2,3,3,3‐tetrafluoropropionate esters. However, γ ‐ and δ‐hydroxyesters did not give their fluorinated compounds. Hydrolysis of those racemic monofluoroesters with Lipase MY gave optical active monofluorocarboxylic acids and esters.