Towards organo-click chemistry: development of organocatalytic multicomponent reactions through combinations of aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions

Chemistry : a European Journal
Dhevalapally B Ramachary, Carlos F Barbas

Abstract

Here we report on our studies on combinations of amino acids and copper(I) for catalyzing multicomponent reactions (MCRs). We aimed to prepare both diene and dienophiles simultaneously, under very mild and environmentally friendly conditions, thus giving the constituents for a stereocontrolled Diels-Alder reaction, which in turn yields compounds 4 to 8. A diversity-oriented synthesis of polysubstituted spirotriones 4 to 6 were assembled from simple substrates like 1-(triphenylphosphanylidene)-propan-2-one, two aldehydes, and cyclic-1,3-diketones through Wittig/Knoevenagel/Diels-Alder and aldol/Knoevenagel/Diels-Alder reaction sequences in one pot under stereospecific organocatalysis. Chemical diversity libraries of polysubstituted spirotrione-1,2,3-traizoles 8 were assembled from simple substrates by means of Wittig/Knoevenagel/Diels-Alder/Huisgen cycloaddition reaction sequences in one pot under stereospecific organo/Cu(I) catalysis. Functionalized dispirolactones such as 6 are biologically active antioxidants and radical scavengers, and spirotrione-1,2,3-traizoles 8 have found wide applications in chemistry, biology, and materials science. Experimentally simple and environmentally friendly, organocatalytic, asymmetric four-co...Continue Reading

References

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Citations

Sep 26, 2012·Organic & Biomolecular Chemistry·Robert N HansonRobert G Croy
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Jinpeng ZhangJie Ding
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Ju-Hua PengGe Zhang
Jan 15, 2014·Amino Acids·Fatemeh TahooriParvin Boloori
Feb 26, 2016·The Journal of Organic Chemistry·Dhevalapally B Ramachary, Kodambahalli S Shruthi
Jun 25, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marco AraújoBeatriu Escuder
Dec 17, 2011·Organic Letters·Penchal Reddy Nandaluru, Graham J Bodwell
Apr 10, 2013·Organic Letters·Nobuyuki Mase, Takuya Horibe
Mar 23, 2011·Journal of the American Chemical Society·Selvanathan Arumugam, Vladimir V Popik
Aug 25, 2011·Journal of the American Chemical Society·Selvanathan Arumugam, Vladimir V Popik
Feb 19, 2005·Angewandte Chemie·Diego J Ramón, Miguel Yus
Jun 20, 2007·Chemical Society Reviews·Daniel M D'Souza, Thomas J J Müller
Apr 14, 2015·Organic & Biomolecular Chemistry·Adluri B Shashank, Dhevalapally B Ramachary
Jun 27, 2006·Chemistry : a European Journal·Rachel K O'ReillyKaren L Wooley
Feb 3, 2007·Organic & Biomolecular Chemistry·Dhevalapally B Ramachary, G Babul Reddy
Nov 30, 2006·Angewandte Chemie·Claudio Palomo, Antonia Mielgo
Dec 30, 2006·Angewandte Chemie·Armando CarloneKarl Anker Jørgensen
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Jun 6, 2008·Organic & Biomolecular Chemistry·Xinhong Yu, Wei Wang
Oct 22, 2008·Organic & Biomolecular Chemistry·C B Shinisha, Raghavan B Sunoj

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