Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5+4) Cycloadditions

被引：22
作者：
Scuiller, Anais [1 ]
Karnat, Alexandre [1 ]
Casaretto, Nicolas [2 ]
Archambeau, Alexis [1 ]
机构：
[1] Ecole Polytech, CNRS, ENSTA ParisTech, Lab Synth Organ,UMR 7652, F-91128 Palaiseau, France
[2] Ecole Polytech, CNRS, Lab Chim Mol, UMR 9168, F-91128 Palaiseau, France
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 06期
关键词：
MEDIUM-SIZED RINGS; METHYLIDENE-DELTA-VALEROLACTONES; ASYMMETRIC CYCLOADDITIONS; ACCESS; CONSTRUCTION; ESTERS;
D O I：
10.1021/acs.orglett.1c00477
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.
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收藏
页码：2332 / 2336
页数：5
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