N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles via Azolium Enolate Intermediates

被引：18

作者：

Li, Sun ^{[1
]}

Chen, Xiang-Yu ^{[1
]}

Sheng, He ^{[1
]}

von Essen, Carolina ^{[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, Finland

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 05期

基金：

欧洲研究理事会;

关键词：

asymmetric synthesis; dihydropyranone thiazole; N-heterocyclic carbene; organocatalysis; 4+2] annulation; DIELS-ALDER REACTIONS; BOND-FORMING REACTIONS; NHC CATALYSIS; NUCLEOPHILIC CARBENES; 4+2 CYCLOADDITION; SALVINORIN-A; ORGANOCATALYSIS; ACTIVATION; ALDEHYDES; ACYL;

D O I：

10.1055/s-0036-1591872

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereo-and enantiostereoselective synthesis of bicyclic dihydropyranothiazoles combining a thiazole and 6-lactone skeleton via NHC-catalyzed [4+2] annulation of 5-alkenylthiazolones and alpha-chloroaldehydes has been developed. The heterocyclic products are formed via azolium enolate intermediates in good yields with high diastereo-and enantistereoselectivities.

引用

页码：1047 / 1052

页数：6

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