A NEW SYNTHESIS OF BOTH THE ENANTIOMERS OF 4-AMINO-3-HYDROXYBUTANOIC ACID (GABOB) AND MM2 CALCULATIONS FOR ROTAMERS OF THE INTERMEDIATE OXAZOLIDIN-2-ONES

被引:61
作者
BONGINI, A [1 ]
CARDILLO, G [1 ]
ORENA, M [1 ]
PORZI, G [1 ]
SANDRI, S [1 ]
机构
[1] CNR, DIPARTIMENTO CHIM G CIAMICIAN, CTR STUDIO FIS MACROMOLEC, I-40126 BOLOGNA, ITALY
关键词
D O I
10.1016/S0040-4020(01)90313-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The easy chromatographic separation of the diastereomeric mixture of oxazolidin-2-ones 4a and 4b allows to synthesize pure R-(-)-1a and (S)-(+)-GABOB 1b. The 1H NMR pattern of 4a and 4b can be correlated with the configuration at C-5 and this relationship is confirmed by MM2 calculations for rotamers of 5-substituted oxazolidin-2-ones.
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页码:4377 / 4383
页数:7
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