SUPRAMOLECULAR ASYMMETRIC INDUCTION - A NEW CONCEPT APPLIED TO THE SUPPORTED ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS

被引：18

作者：

CALMES, M ^{[1
]}

DAUNIS, J ^{[1
]}

ISMAILI, H ^{[1
]}

JACQUIER, R ^{[1
]}

KOUDOU, J ^{[1
]}

NKUSI, G ^{[1
]}

ZOUANATE, A ^{[1
]}

机构：

[1] UNIV MONTPELLIER 2,URA 468,SYNTH & ETUD PHYSICOCHIM AMINOACIDES & PEPTIDES LAB,PL E BATAILLON,F-34095 MONTPELLIER 5,FRANCE

来源：

TETRAHEDRON | 1990年 / 46卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(01)87926-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A polyacrylic resin with pendant chirality has been used as a chiral auxiliary. The prochiral ester enolate, reversibly linked to the polymer chain via a Schiff base, is surrounded by chiral pendants, allowing supramolecular asymmetric induction to occur. Amino acids with enantiomeric excesses up to 88-89% could be synthesized from supported glycine t-butyl ester enolate by reaction with alkyl halides. Enantioselective protonation depends on the initial configuration of the supported aminoacid. Alanine was obtained in 90% ee by repetitive asymmetric protonation. © 1990.

引用

页码：6021 / 6032

页数：12

共 76 条

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