TUNABLE STEREOSELECTIVITY IN THE ADDITION OF 2-LITHIOTHIAZOLE TO L-SERINAL DERIVED N-BENZYL NITRONE - SYNTHESIS OF C-2 EPIMER 2,3-DIAMINO-4-HYDROXYBUTANALS

被引:34
作者
DONDONI, A
MERCHAN, FL
MERINO, P
TEJERO, T
BERTOLASI, V
机构
[1] UNIV FERRARA,DIPARTMENTO CHIM,CHIM ORGAN LAB,I-44100 FERRARA,ITALY
[2] UNIV FERRARA,CTR STRUTTURIST DIFFRATTOMETR,FERRARA,ITALY
[3] UNIV ZARAGOZA,ICMA,DEPT QUIM ORGAN,ZARAGOZA,SPAIN
关键词
D O I
10.1039/c39940001731
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A complete reversal of diastereoselectivity (ds greater than or equal to 95%) in the addition of 2-lithiothiazole to L-serinal derived N-benzyl nitrone has been achieved by the change of the hydroxy and amino protective groups in the aldehyde moiety; the resultant epimeric 2-thiazolyl N-benzyl hydroxylamines were converted to C-2 epimer 2,3-diamino-4-hydroxybutanals via reductive dehydroxylation and thiazolyl-to-formyl conversion.
引用
收藏
页码:1731 / 1733
页数:3
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