Chemoenzymatic synthesis of both enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one

被引：17

作者：

Demir, AS ^{[1
]}

Aybey, A ^{[1
]}

Sesenoglu, Ö ^{[1
]}

Polat, F ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(03)00214-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

4-Oxo-3,4-dihydro-2-chromen-3-yl acetate is synthesized using manganese(III)acetate starting from 2,3-dihydro-4H-chromen-4-one. K2CO3 mediated hydrolysis of 4-oxo-3,4-dihdro-2-chromen-3-yl acetate furnished 3-hydroxy-2,3-dihydro-4H-chromen-4-one in high yield. The enantioselective hydrolysis of (+/-)-4-oxo-3,4-dihydro-2-chromen-3-yI acetate in various organic solvent-phosphate buffer (pH7) systems and enantioselective transesterification of (+/-)-3-hydroxy-2,3-dihydro-4H-chromen-4-one in organic solvents was investigated by screening a range of lipases. The lipase Amano PS, PPL, PLE and CCL-catalyzed asymmetric ester hydrolysis and transesterification afforded the enantiomers of 3-hydroxy-2,3-dihydro-4H-chromen-4-one and 4-oxo-3,4-dihydro-2-chromen-3-yI acetate with high enantiomeric excess (up to 97% ee) and in good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1489 / 1493

页数：5

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