Dynamic Kinetic Asymmetric Transformation (DYKAT) by Combined Amine- and Transition-Metal-Catalyzed Enantioselective Cycloisomerization

被引:85
作者
Zhao, Gui-Ling [1 ]
Ullah, Farman [1 ]
Deiana, Luca [1 ]
Lin, Shuangzheng [1 ]
Zhang, Qiong [4 ]
Sun, Junliang [2 ,3 ]
Ibrahem, Ismail [1 ]
Dziedzic, Pawel [1 ]
Cordova, Armando [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
[2] Stockholm Univ, Arrhenius Lab, Dept Struct Chem, S-10691 Stockholm, Sweden
[3] Stockholm Univ, Arrhenius Lab, Berzelii Ctr EXSELENT Porous Mat, S-10691 Stockholm, Sweden
[4] Royal Inst Technol, Dept Theoret Chem, Sch Biotechnol, S-10691 Stockholm, Sweden
关键词
asymmetric synthesis; cyclopentenes; dynamic kinetic transformation; organocatalysis; transition-metal catalysis; PHASE-TRANSFER CATALYST; ONE-POT SYNTHESIS; ALLYLIC ALKYLATION; ALPHA; BETA-UNSATURATED ALDEHYDES; DOMINO REACTIONS; QUATERNARY STEREOCENTERS; CASCADE CATALYSIS; ORGANIC-SYNTHESIS; ALDER REACTIONS; ALDOL REACTIONS;
D O I
10.1002/chem.200902818
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first examples of one-pot highly chemo- and enantioselective dynamic kinetic asymmetric transformations (DYKATs) involving alpha,beta-unsaturated aldehydes and proparaylated carbon acids are presented. These DYKATs, which proceed by a combination of catalytic iminium activation, enamine activation, and Pd-0-catalyzed enyne cycloisomerization, give access to functionalized cyclopentenes wit. It up to. 99% ee and can be used for the generation of all-carbon quaternary stereocenters
引用
收藏
页码:1585 / 1591
页数:7
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