PETERSON OLEFINATION REACTION USING (TRIMETHYLGERMYL)ACETATE - STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENOIC ACID-ESTERS

被引:11
作者
INOUE, S [1 ]
SATO, Y [1 ]
机构
[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN
关键词
D O I
10.1021/jo00001a064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Peterson-type reaction of (trimethylgermyl)acetates 1 with aldehydes and ketones 2 gave stereoselectively (E)-2-alkenoic acid esters (E)-4 after stirring at -78-degrees-C and warming to room temperature. High yields of the reaction intermediates threo- and erythro-3-hydroxy-2-(trimethylgermyl)alkanoic acid esters 3 were obtained when the reaction was quenched at -78-degrees-C. The paths for conversion of threo-3 and erythro-3 to (E)-4 are discussed.
引用
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页码:347 / 352
页数:6
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