SYNTHESIS OF OPTICALLY-ACTIVE SUBSTITUTED CYCLOHEXENONES FROM CARBOHYDRATES BY CATALYTIC FERRIER REARRANGEMENT

被引:61
作者
CHIDA, N [1 ]
OHTSUKA, M [1 ]
OGURA, K [1 ]
OGAWA, S [1 ]
机构
[1] KEIO UNIV, FAC SCI & TECHNOL, DEPT APPL CHEM, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN
关键词
D O I
10.1246/bcsj.64.2118
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conversion of hex-5-enopyranosides into substituted cyclohexanones (Ferrier rearrangement) was found to proceed efficiently with a catalytic amount of various mercury(II) salts at room temperature in a neutral solvent system. Among the mercury(II) salts tested, mercury(II) trifluoroacetate showed the highest activity. Four optically active cyclohexenones were prepared from hex-5-enopyranosides utilizing this method.
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页码:2118 / 2121
页数:4
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