Dynamic Kinetic Asymmetric Domino Oxa-Michael/Carbocyclization by Combination of Transition-Metal and Amine Catalysis: Catalytic Enantioselective Synthesis of Dihydrofurans

被引：65

作者：

Lin, Shuangzheng ^{[1
]}

Zhao, Gui-Ling ^{[1
,2
]}

Deiana, Luca ^{[1
,2
]}

Sun, Junliang ^{[2
,3
]}

Zhang, Qiong ^{[4
]}

Leijonmarck, Hans ^{[1
,2
]}

Cordova, Armando ^{[1
,2
,5
]}

机构：

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

[2] Stockholm Univ, Berzelii Ctr EXSELENT Porous Mat, Arrhenius Lab, S-10691 Stockholm, Sweden

[3] Stockholm Univ, Dept Struct Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

[4] Royal Inst Technol, Dept Theoret Chem, Sch Biotechnol, S-10691 Stockholm, Sweden

[5] Mid Sweden Univ, Dept Nat Sci Engn & Math, S-85170 Sundsvall, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 47期

关键词：

asymmetric catalysis; co-catalysis; domino reactions; furans; palladium; ONE-POT SYNTHESIS; ALLYLIC ALKYLATION; FORMAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CASCADE CATALYSIS; ENOL ETHERS; ALDEHYDES; PALLADIUM; CYCLIZATIONS; IMINIUM;

D O I：

10.1002/chem.201001992

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13930 / 13934

页数：5

共 5 条

[1] Catalytic enantioselective domino oxa-Michael/aldol condensations:: Asymmetric synthesis of benzopyran derivatives
Sunden, Henrik
Ibrahem, Ismail
Zhao, Gui-Ling
Eriksson, Lars
Cordova, Armando
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) : 574 - 581
[2] Catalytic Asymmetric Domino Michael Addition-Alkylation Reaction: Enantioselective Synthesis of Dihydrofurans
Rueping, Magnus
Parra, Alejandro
Uria, Uxue
Besselievre, Francois
Merino, Estibaliz
[J]. ORGANIC LETTERS, 2010, 12 (24) : 5680 - 5683
[3] Enantioselective Synthesis of Spiro Heterocyclic Compounds Using a Combination of Organocatalysis and Transition-Metal Catalysis
Kamlar, Martin
Urban, Michal
Vesely, Jan
[J]. CHEMICAL RECORD, 2023, 23 (07):
[4] Enantioselective Synthesis of 2,6-cis-Disubstituted Tetrahydropyrans via a Tandem Catalytic Asymmetric Hydrogenation/Oxa-Michael Cyclization: An Efficient Approach to (-)-Centrolobine
Xie, Jian-Hua
Guo, Lu-Chuan
Yang, Xiao-Hui
Wang, Li-Xin
Zhou, Qi-Lin
[J]. ORGANIC LETTERS, 2012, 14 (18) : 4758 - 4761
[5] Dynamic Kinetic Asymmetric Transformation (DYKAT) by Combined Amine- and Transition-Metal-Catalyzed Enantioselective Cycloisomerization
Zhao, Gui-Ling
Ullah, Farman
Deiana, Luca
Lin, Shuangzheng
Zhang, Qiong
Sun, Junliang
Ibrahem, Ismail
Dziedzic, Pawel
Cordova, Armando
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1585 - 1591

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