手性硫脲催化异丁醛和β-硝基苯乙烯的不对称迈克尔加成反应研究  

Chiral thiourea catalyzed asymmetric Michael addition reaction of Ⅰ sobutyraldehyde and β-nitrostyrene

作　　者：戴利[1] 王海豹[1] 蒋广敏 DAI Li;WANG Hai-bao;JING Guang-min(Zaozhuang Vocational College of Science and Technology,Zaozhuang 277500,China;Tengzhou secondary vocational education center school,Zaozhuang 277500,China)

机构地区：[1]枣庄科技职业学院,山东枣庄277500 [2]滕州市中等职业教育中心学校,山东枣庄277500

出　　处：《枣庄学院学报》2020年第2期9-14,共6页Journal of Zaozhuang University

摘　　要：本文合成了N-[(1S,2S)-2-氨基环己基]-N'-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖)硫脲,并将它用于催化异丁醛和β-硝基苯乙烯的迈克尔加成反应,研究了不同催化剂用量、不同的异丁醛当量对反应的影响.在优化的条件下,反应得到了(82%~94%)收率和(92%~99%ee)对映选择性;把此催化剂用于催化不同取代的β-硝基苯乙烯和异丁醛反应,也获得了非常好的收率(68%~94%)和对映选择性(97%~99.3%ee).IN this paper,N-[(1s,2S)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea was synthesized and used to catalyze the Michael addition reaction of isobutyraldehyde andβ-nitrostyrene.The effects of different catalyst dosage and isobutyraldehyde equivalent on the reaction were studied.Under optimized conditions,the yield(82%~94%)and enantioselectivity(92%~99%ee)were obtained.The catalyst has also been used to catalyze the reaction of different substitutedβ-nitrostyrene and isobutyraldehyde with very good yields(68%~94%)and enantioselectivity(97%~99.3%ee).

关 键 词：不对称加成 迈克尔反应 有机催化 

分 类 号：O621[理学—有机化学]