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化学学报
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化学学报 ›› 1987, Vol. 45 ›› Issue (10): 997-1001. 上一篇    下一篇

研究论文

固-液相转移催化合成V.醛亚胺的michael加成和羰基加成反应合成α-氨基 酸

邬胜德;周昌友;刘桂兰;邓润华;蒋耀忠   

  1. 中国科学院成都有机化学研究所
  • 发布日期:1987-10-15

Solid-liquid phase transfer catalytic synthesis V. Michael addition , carbonyl addition reactions of aldimines for the synthesis of \a\-amino acids

WU SHENGDE;ZHOU CHANGYOU;LIU GUILAN;DENG RUNHUA;JIANG YAOZHONG   

  • Published:1987-10-15

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623

被引次数

19

报道了在以K~2CO~2为固体碱的固-液相转移催化条件下,用醛亚胺与亲电的 烯烃和醛类化合物进行Michael加成,羰基加成反应,合成了一系列醛亚胺亲核加成产物.并通过水解羰基加成产物制备了一系列丝氨酸衍生物.该法简便,温和,反应时间短,产率高,是合成具有取代基的甘氨酸,丙氨酸和丝氨酸及其酯的一种有用方法.

关键词: 氨基酸, 水解, 烯烃, 碳酸钾, 相转移催化, 丙氨酸, 醛, 加成反应, 甘氨酸, 丝氨酸

Michael addition of 4-R1C6H4CH:NCHR2CO2R3 (I; R1 = H, Cl; R2 = H, Me; R3 = Me, Et) with R4CH:CHR5 (R4 = H, Ph; R5 = CO2Me, cyano), PhCH2NEt3Cl, K2CO3 in MeCN gave 4-R1C6H4CH:NCR2(CO2R3)CHR4CH2R5. Addition reaction of I (R1 = Cl, R2 = H, Me, R3 = Me, Et) with R6CHO (R6 = H, Ph, 4-ClC6H4, 4-O2NC6H4) gave oxazolidines II, hydrolysis of which gave R6CH(OH)CR2(NH2)CO2H.

Key words: AMINO ACID, HYDROLYSIS, ALKENE, POTASSIUM CARBONATE, PHASE TRANSFER CATALYSIS, ALANINE, ALDEHYDES, ADDITION REACTION, GLYCINE, SERINE

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