ASYMMETRIC-SYNTHESIS OF KETOPROFEN - A SURPRISING BASE CATALYST EFFECT DURING ASYMMETRIC ADDITION OF PANTOLACTONE TO METHYL (3-BENZOYLPHENYL) KETENE

被引：25

作者：

CALMES, M

DAUNIS, J

JACQUIER, R

NATT, F

机构：

[1] Laboratoire des Amino Acides et Peptides, URA 468 - Université Montpellier II, Place E. Bataillon

来源：

TETRAHEDRON | 1994年 / 50卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)81339-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The best diastereoselectivity of addition of a chiral alcohol to the ketene derived from ketoprofen was obtained with R or S pantolactone (ed=99%). 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 99%.

引用

页码：6875 / 6880

页数：6

共 33 条

[1] SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL ALPHA-L-IDOPYRANOSIDURONIC ACID [J].