A CHEMOENZYMATIC APPROACH TO CHIRAL PHENYLISOSERINATES USING 4-ISOPROPYL-2-OXAZOLIN-5-ONE AS MASKED UMPOLED SYNTHON FOR HYDROXYCARBONYL ANION

被引：18

作者：

BARCO, A ^{[1
]}

BENETTI, S ^{[1
]}

DERISI, C ^{[1
]}

POLLINI, GP ^{[1
]}

ROMAGNOLI, R ^{[1
]}

ZANIRATO, V ^{[1
]}

机构：

[1] UNIV FERRARA,DIPARTIMENTO SCI FARMACEUT,I-44100 FERRARA,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 49期

关键词：

D O I：

10.1016/0040-4039(94)88490-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol adduct between the anion of 4-isopropyl-2-oxazolin-5-one with racemic N-(tert-butoxycarbonyl)-phenylglycinal underwent concomitant isomerization and ring cleavage under mild basic conditions producing the racemic dipeptide N-Boc-phenylisaserine-valine methyl ester, which after acid hydrolysis followed by sequential esterification and N-benzoylation, gave a separable 1:4 syn/anti diasteroisomeric mixture of N-benzoyl-3-phenylisoserine methyl esters, the predominant anti racemate being resolved by lipase from Pseudomonas fluorescens (P) using vinyl acetate as the acyl donor leading to the corresponding chiral phenylisoserine derivatives.

引用

页码：9289 / 9292

页数：4

共 27 条

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