Sc(OTf)3-Catalyzed Cyclization of Allyl Amides of Ethenetricarboxylate
Sc(OTf)3-Catalyzed Cyclization of Allyl Amides of Ethenetricarboxylate
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Sc(OTf)3-催化乙烯三羧酸烯丙基酰胺的环化
DOI：
10.1055/s-0035-1561643
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发表时间：
2016
期刊：
影响因子：
--
通讯作者：
K.
中科院分区：
文献类型：
--
作者：
Yamazaki;S; Niina;M.; Kakiuchi;K.
研究了乙烯三羧酸烯丙酰胺催化环化生成吡咯烷的反应。乙烯三羧酸的烯丙基酰胺与Sc（OTf）3（0.2当量）反应得到作为主要产物的4-羟甲基-2-氧代吡咯烷衍生物。羟甲基吡咯烷的形成可能是由于外来水的原位参与。在Sc（OTf）3催化下，烯丙基酰胺与TMSX（X = Cl，Br）发生环化反应，得到卤代2-氧代吡咯烷衍生物。Sc（OTf）3催化的烯丙基酯与TMSX（X= Cl，Br）的环化反应也得到卤代2-氧代四氢呋喃衍生物。
Catalytic cyclization of allyl amides of ethenetricarboxylate leading to pyrrolidines has been examined. Reaction of allyl amides of ethenetricarboxylate with Sc(OTf)3(0.2 equiv) gave 4-hydroxymethyl-2-oxopyrrolidine derivatives as major products. The formation of hydroxymethylpyrrolidines may arise from participation of adventitious water in situ. Sc(OTf)3-catalyzed cyclization reactions of the allyl amides with TMSX (X = Cl, Br) proceeded efficiently to give halogenated 2-oxopyrrolidine derivatives. Sc(OTf)3-catalyzed cyclization reactions of the allyl ester with TMSX (X= Cl, Br) also proceeded to give halogenated 2-oxotetrahydrofuran derivatives.