Literature DB >> 21322637

Enantioselective organocatalytic aza-ene-type domino reaction leading to 1,4-dihydropyridines.

Artur Noole1, Maria Borissova, Margus Lopp, Tõnis Kanger.   

Abstract

A new general methodology was developed to access highly enantiomerically enriched 1,4-dihydropyridines (DHPs) 3 via an organocatalytic asymmetric aza-ene-type cascade reaction, cocatalyzed by (S)-diarylprolinol-TMS ether V and benzoic acid (BA). Both aliphatic and aryl enals 1 reacted smoothly with enaminones and β-enamino esters 2, affording highly functionalized 1,4-DHPs 3 in high enantioselectivities and good yields.

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Year:  2011        PMID: 21322637     DOI: 10.1021/jo200095e

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Efficient synthesis of functionalized spiro[indoline-3,4'-pyrrolo[3,4-b]pyridines] via one-pot three-component reaction.

Authors:  Chao Wang; Yan-Hong Jiang; Chao-Guo Yan
Journal:  Mol Divers       Date:  2014-07-31       Impact factor: 2.943

2.  Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones.

Authors:  Sergei Zari; Tiiu Kailas; Marina Kudrjashova; Mario Oeren; Ivar Järving; Toomas Tamm; Margus Lopp; Tõnis Kanger
Journal:  Beilstein J Org Chem       Date:  2012-09-04       Impact factor: 2.883

3.  A chemoselective route to β-enamino esters and thioesters.

Authors:  Dongyue Xin; Kevin Burgess
Journal:  Org Lett       Date:  2014-03-31       Impact factor: 6.005

4.  Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes.

Authors:  Krzysztof Dzieszkowski; Izabela Barańska; Zbigniew Rafiński
Journal:  J Org Chem       Date:  2020-04-29       Impact factor: 4.354

  4 in total

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