STEREODIVERGENT SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS DERIVED FROM L-QUEBRACHITOL

被引:33
作者
AKIYAMA, T
NISHIMOTO, H
KUWATA, T
OZAKI, S
机构
关键词
D O I
10.1246/bcsj.67.180
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reduction of an alpha-keto ester derived from chiral cyclitol, readily available from L-quebrachitol, with K-Selectride proceeded via re-face attack of the ketone with high diastereoselectivity to obtain the alpha-hydroxy ester in 92% de. On the other hand, reduction of the alpha-keto ester with K-Selectride in the presence of 18-Crown-6 took place via si-face attack of the ketone to furnish the corresponding alpha-hydroxy ester in 92% de. Thus both enantiomers of mandelic acid were obtained in optically pure form.
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页码:180 / 188
页数:9
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