Tetrahedron p. 6875 - 6880 (1994)
Update date:2022-08-03
Topics: Asymmetric synthesis Base Catalyst Asymmetric addition Pantolactone
Calmes, Monique
Daunis, Jacques
Jacquier, Robert
Natt, Francois
The best diastereoselectivity of addition of a chiral alcohol to the ketene derived from ketoprofen was obtained with R or S pantolactone (ed=99percent).Depending on the tertiary amine used both for ketene formation and as catalyst during addition, the diastereoisomeric ratio of esters could be strongly modified and even inverted.Mild saponification afforded R or S ketoprofen in enantiomeric excess of up to 99percent.
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