Thiazole, Imidazole and Oxazoline Based N,P-Ligands for Palladium-Catalyzed Cycloisomerization of 1,6-Enynes

被引：6

作者：

Quan, Xu ^{[1
]}

Liu, Jianguo ^{[1
]}

Rabten, Wangchuk ^{[1
,2
]}

Diomedi, Simone

Singh, Thishana ^{[3
]}

Andersson, Pher G. ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[2] Univ Camerino, Div Chem, Sch Sci & Technol, I-62032 Camerino, Italy

[3] Durban Univ Technol, Dept Chem, ZA-4000 Durban, South Africa

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 20期

基金：

瑞典研究理事会;

关键词：

Cyclization; Isomerization; Enynes; N; P ligands; Palladium; Density functional calculations; ENE-TYPE CYCLIZATION; ASYMMETRIC HYDROGENATION; (Z)-4'-ACETOXY-2'-BUTENYL 2-ALKYNOATES; ENANTIOSELECTIVE SYNTHESIS; IRIDIUM CATALYSTS; SPIRO-CYCLIZATION; ALLYLIC ALCOHOLS; LIGANDS; ISOMERIZATION; COMPLEXES;

D O I：

10.1002/ejoc.201600468

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N,P-ligands were prepared and evaluated in the asymmetric palladium-catalyzed cycloisomerization of allyl propargyl ether substrates. The reactivity and enantioselectivity of the reaction was shown to be highly dependent on the chiral skeleton of the ligand structures with ee's ranging from 22-99 %. The proton source had a significant impact on the enantioselectivity. The generation of palladium hydride from formic acid led to the highest ee. A selectivity model based on a proposed transition state was used to predict and explain the enantiomeric outcome of the reaction.

引用

页码：3427 / 3433

页数：7

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