Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts

被引：13

作者：

Ma, Guangning ^{[1
]}

Lin, Shuangzheng ^{[2
]}

Ibrahem, Ismail ^{[1
]}

Kubik, Grzegorz ^{[2
]}

Liu, Leifeng ^{[3
,4
]}

Sun, Junliang ^{[3
,4
]}

Cordova, Armando ^{[1
,2
,3
]}

机构：

[1] Mid Sweden Univ, Dept Nat Sci Engn & Math, SE-85170 Sundsvall, Sweden

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

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

[4] Stockholm Univ, Dept Mat & Environm Chem, Arrhenius Lab, S-10691 Stockholm, Sweden

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 14-15期

关键词：

cascade reactions; deracemization; dynamic asymmetric catalysis; hydrogen-bond donor; organocatalysis; reactions on racemic mixtures; stereodivergence; HIGHLY ENANTIOSELECTIVE CATALYST; ORGANIC-SYNTHESIS; TRANSFORMATIONS DYKAT; POLYKETIDE SUGARS; MICHAEL ADDITION; DOMINO REACTIONS; ACID; ALDEHYDES; ALDOL; POT;

D O I：

10.1002/adsc.201200357

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic ?-nitro ketones and a,beta-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

引用

页码：2865 / 2872

页数：8