Organocatalytic Enantioselective Aziridination of α-Substituted α,β-Unsaturated Aldehydes: Asymmetric Synthesis of Terminal Aziridines

被引：42

作者：

Deiana, Luca ^{[1
,2
]}

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

Lin, Shuangzheng ^{[1
]}

Dziedzic, Pawel ^{[1
,2
]}

Zhang, Qiong ^{[4
]}

Leijonmarck, Hans ^{[1
,2
]}

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

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

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 18期

关键词：

asymmetric catalysis; domino reactions; organocatalysis; alpha-substituted alpha; beta-unsaturated aldehydes; terminal aziridines; SILYL ENOL ETHERS; CATALYTIC AZIRIDINATION; CHIRAL AZIRIDINES; SULFUR YLIDES; AMINO-ACIDS; OLEFINS; CYCLOPROPANATION; COMPLEXES; EPOXIDES; ALCOHOLS;

D O I：

10.1002/adsc.201000650

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first example of a highly enantioselective organocatalytic aziridination of alpha-substituted alpha,beta-unsaturated aldehydes is presented. The reaction is catalyzed by simple chiral amines and gives access to highly functional terminal azirdines containing an alpha-tertiary amine stereocenter in high yields and enantiomeric ratios (95.5:4.5-98:2).

引用

页码：3201 / 3207

页数：7

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