Rh-Catalyzed Cycloisomerization of 1,7-Ene-Dienes to Synthesize trans-Divinylpiperidines: A Formal Intramolecular Addition Reaction of Allylic C-H Bond into Dienes

被引：10

作者：

Cui, Qi ^{[1
]}

Liao, Wei ^{[1
]}

Tian, Zi-You ^{[1
]}

Li, Qian ^{[1
]}

Yu, Zhi-Xiang ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn,BNLMS, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 19期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; 4+2 CYCLOADDITION; ACTIVATION; MECHANISM; SYSTEM;

D O I：

10.1021/acs.orglett.9b02319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An originally designed Rh-catalyzed [4 + 2] cycloaddition reaction of nitrogen-tethered 1,7-ene-dienes turned out to be a cycloisomerization reaction, which involves allylic C-H activation/alkene insertion into Rh-H bond/reductive elimination processes. Deuterium labeling experiments gave support to the proposed mechanism. This unexpected cycloisomerization reaction provides an efficient way to synthesize trans-divinylpiperidines from easily accessed linear 1,7-ene-dienes.

引用

页码：7692 / 7696

页数：5

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