Regioselective [2+2+2] Cycloaddition Reaction Using Allene-ynes with Simple Allenes under Nickel Catalysis

被引：8
|
作者：
Arai, Shigeru [1 ,2 ]
Izaki, Arisa [1 ]
Amako, Yuka [1 ]
Nakajima, Masaya [1 ,4 ]
Uchiyama, Masanobu [3 ,4 ]
Nishida, Atsushi [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba, Japan
[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba, Japan
[3] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo, Japan
[4] RIKEN, Adv Elements Chem Lab, CPR, 2-1 Hirosawa, Wako, Saitama, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 21期
基金：
日本学术振兴会;
关键词：
allene; catalysis; cycloaddition; nickel; regioselective; RHODIUM(I)-CATALYZED CYCLOISOMERIZATION; ENANTIOSELECTIVE SYNTHESIS; ALKENYLATIVE CYCLIZATIONS; INTERMOLECULAR 5+2; ENE-ALLENES; ALKYNES; CHEMOSELECTIVITY; VINYLCYCLOPROPANES; HYDROSILYLATION; ANNULATION;
D O I：
10.1002/adsc.201900719
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A Ni-catalyzed [2+2+2] cycloaddition reaction between allene-ynes and various mono-, di- and tri-substituted allenes is described. This protocol effectively differentiates allenyl pi components and shows broad substrate generality to give highly functionalized carbocycles. A DFT study played a key role in revealing a detailed reaction mechanism that controls site-, regio- and stereoselectivity, which are thought to originate in the substituent effect on pi-bonds in the early transition state.
引用
收藏
页码：4882 / 4887
页数：6
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