N-Heterocyclic Carbene-Catalyzed Activation of -Chloroaldehydes: Asymmetric Synthesis of 5-Cyano-Substituted Dihydropyranones

被引：5

作者：

Li, Sun ^{[1
]}

Chen, Xiang-Yu ^{[1
]}

Liu, Qiang ^{[1
]}

Peuronen, Anssi ^{[2
]}

Rissanen, Kari ^{[2
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, Jyvaskyla 40014, Jyu, Finland

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 21期

基金：

欧洲研究理事会;

关键词：

dihydropyranones; asymmetric synthesis; organocatalysis; N-heterocyclic carbenes; -chloroaldehydes; DIELS-ALDER REACTIONS; BOND-FORMING REACTIONS; ENANTIOSELECTIVE SYNTHESIS; ALPHA-CHLOROALDEHYDES; NUCLEOPHILIC CARBENES; 4+2 CYCLOADDITION; NHC CATALYSIS; ORGANOCATALYSIS; ALDEHYDES; EQUIVALENTS;

D O I：

10.1055/s-0036-1588509

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-heterocyclic carbene (NHC)-catalyzed asymmetric [4+2] annulation of (E)-2-benzoyl-3-phenylacrylonitriles with alpha-chloroaldehydes has been developed. The protocol leads to 5-cyano-substituted dihydropyranones in good to excellent yields with excellent diastereo- and enantioselectivities (up to 93% yield, >20:1 d.r. and 99% ee).

引用

页码：4861 / 4868

页数：8

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