Lewis Acid Catalyzed Cyclization Reactions of Ethenetricarboxylates via Intramolecular Hydride Transfer

被引：14

作者：

Yamazaki, Shoko ^{[1
]}

Naito, Taku ^{[1
]}

Niina, Mamiko ^{[1
]}

Kakiuchi, Kiyomi ^{[2
]}

机构：

[1] Nara Univ Educ, Dept Chem, Takabatake Cho, Nara 6308528, Japan

[2] Nara Inst Sci & Technol NAIST, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 13期

关键词：

PROMOTED CYCLIZATION; FUNCTIONALIZATION; DERIVATIVES; AMINATION;

D O I：

10.1021/acs.joc.7b00895

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic cyclization of amides of ethenetricarboxylate bearing ether and acetal groups has been examined. The reaction of the amides bearing cyclic ether and acetal in groups the presence of Lewis acid such as Sc(OTf)(3) gave spirocyclic piperidine derivatives as major products. The cydized products may be formed via intramolecular hydride transfer. The reaction mechanism was examined by the DFT calculations. The scope and limitations of the hydride transfer/cyclization reactions of amides of ethenetricarboxylates was investigated, and morpholine formation by intramolecular oxy-Michael addition was also found.

引用

页码：6748 / 6763

页数：16

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