CATALYTIC KINETIC RESOLUTION OF 5-ALKOXY-2(5H)-FURANONES

被引：32

作者：

FABER, WS ^{[1
]}

KOK, J ^{[1
]}

DELANGE, B ^{[1
]}

FERINGA, BL ^{[1
]}

机构：

[1] UNIV GRONINGEN,GRONINGEN CTR CATALYSIS & SYNTHESIS,DEPT ORGAN & MOLEC INORGAN CHEM,9747 AG GRONINGEN,NETHERLANDS

来源：

TETRAHEDRON | 1994年 / 50卷 / 16期

关键词：

D O I：

10.1016/S0040-4020(01)85016-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1-4-addition of arylthiols, was examined. Using various butenolides it was shown that a gamma-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.

引用

页码：4775 / 4794

页数：20

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