Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions

被引：57

作者：

Wang, Lei ^{[1
]}

Li, Sun ^{[1
]}

Chauhan, Pankaj ^{[1
]}

Hack, Daniel ^{[1
]}

Philipps, Arne R. ^{[1
]}

Puttreddy, Rakesh ^{[2
]}

Rissanen, Kari ^{[2
]}

Raabe, Gerhard ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

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

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 15期

关键词：

asymmetric synthesis; chromenedione; multicomponent reaction; N-heterocyclic carbene; spiropyrazolone; N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; BRONSTED ACID; ACTIVATION; ORGANOCATALYSIS; PYRAZOLONES; DERIVATIVES; PROGRESS; KETONES;

D O I：

10.1002/chem.201600515

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel one-pot, three-component diastereo- and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate ,-unsaturated pyrazolones, which react with a second equivalent of enal through an N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones are obtained in moderate to good yields and good to excellent stereoselectivities. Alternatively, starting from cyclic 1,3-diketones, 2,5-chromenediones are available through [2+4] annulation.

引用

页码：5123 / 5127

页数：5

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