Multiple Multicomponent Reactions with Isocyanides

Wessjohann, Ludger A.; Filho, Ricardo A. W. Neves; Rivera, Daniel G.

doi:10.1002/9783527652532.ch7

Cited by 23 publications

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“…32 Recently, the use of the P-3CR and the U-4CR in polymer chemistry was demonstrated by our [34][35][36][37][38][39] and other groups. [40][41][42][43] Furthermore, sequential Ugi reactions were studied by Wessjohann et al for the synthesis of peptide-peptoid 60 chimeras 31,44,45 and in the synthesis of macrocycles. 31,46 The Passerini reaction is a one-pot reaction of a carboxylic acid with an oxo component (aldehyde or ketone) and an isocyanide, leading to α-acyloxy carboxamides, 47 whereas in the U-4CR, the fourth component is an amine and the obtained products are 65 α-aminoacylamides ( Figure 1).…”

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“…[40][41][42][43] Furthermore, sequential Ugi reactions were studied by Wessjohann et al for the synthesis of peptide-peptoid 60 chimeras 31,44,45 and in the synthesis of macrocycles. 31,46 The Passerini reaction is a one-pot reaction of a carboxylic acid with an oxo component (aldehyde or ketone) and an isocyanide, leading to α-acyloxy carboxamides, 47 whereas in the U-4CR, the fourth component is an amine and the obtained products are 65 α-aminoacylamides ( Figure 1). 28 Compared to the P-3CR, the U-4CR thus offers the possibility to introduce two different side chains in one single reaction step.…”

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Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

2015

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The synthesis of sequence-defined oligomers by the iterative application of the modular Ugi four-component reaction (U-4CR) and the efficient thiol-ene addition reaction is described. By varying the amine component in the U-4CR, a sequence-defined and monodisperse tetramer (M = 1568.5 10 g/mol) was obtained. More interestingly, if both the amine and the isocyanide components were varied simultaneously in the U-4CR, a double sequence-controlled, monodisperse pentamer (M = 2411.8 g/mol) bearing ten different and selectable side chains was obtained. All oligomers were 15 thoroughly characterized by NMR and IR spectroscopy, mass spectrometry and GPC.One of the most challenging topics of modern polymer chemistry is the control over the monomer sequence in synthetic polymers. 1 These highly defined synthetic polymers exhibit novel material 20 properties and special self-assembly behaviour, depending on the monomer sequence. 2 However, the most sophisticated and controlled monomer sequences are synthesized by nature, for instance in translation and replication processes. 3 Over the past decades, different approaches have been developed in order to 25 synthesize sequence-defined polymers. 1,4 On the one hand, controlled radical polymerizations like RAFT, 5-7 ATRP 8-11 and NMP 11-13 can be applied for the synthesis of sequence-controlled polymers. 14 These radical polymerizations take advantage of simple one-pot procedures, but due to the radical nature of those 30 methods, side reactions, such as chain transfer, occur, thus chain to chain deviations are present. 15 On the other hand, stepwise procedures providing monodisperse macromolecules by using (DNA)-templates, [16][17][18][19][20][21] or complex molecular machines are reported. 22, 23 Although these approaches are elegant, the 35 synthetic efforts are considerable and the reactions can only be carried out on small scales. Recently, other protocols for the stepwise synthesis of sequence-defined polymers were reported making use of orthogonal reactions providing sequence-defined macromolecules by the iterative application of Michael additions 40 and aminolysis reactions, 24 azide-alkyne cycloadditions and amidifications, 25 or photochemical couplings and retro Diels-Alder reactions. 26 Our group focusses on the use of multicomponent reactions to achieve sequence control. 27 The iterative application of the Passerini three-component reaction 45

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Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

2015

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“…With respect to 4: The well-planned combination of MCRs (unions) [ 170 , 182 , 183 , 184 , 185 ] opens up a further method for reducing the number of synthesis steps with simultaneous structural assembly based on a modular building concept, such as Scheme 18 .…”

Section: Multicomponent Chemistry—the Futurementioning

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Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Eckert

2017

Molecules

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Several novel methods, catalysts and reagents have been developed to improve organic synthesis. Synergistic effects between reactions, reagents and catalysts can lead to minor heats of reaction and occur as an inherent result of multicomponent reactions (MCRs) and their extensions. They enable syntheses to be performed at a low energy level and the number of synthesis steps to be drastically reduced in comparison with ‘classical’ two-component reactions, fulfilling the rules of Green Chemistry. The very high potential for variability, diversity and complexity of MCRs additionally generates an extremely diverse range of products, thus bringing us closer to the aim of being able to produce tailor-made and extremely low-cost materials, drugs and compound libraries.

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“…With respect to 4: The well-planned combination of MCRs (unions) [172,[186][187][188][189] opens up a further method for reducing the number of synthesis steps with simultaneous structural assembly based on a modular building concept, such as Scheme 18.…”

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Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Eckert

2017

Preprint

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Synergistic effects between reactions, reagents and catalysts can lead to minor heats of reaction and occur as an inherent result of multi-component reactions (MCRs) and their extensions. They enable syntheses to be performed at a low energy level and the number of synthesis steps to be drastically reduced in comparison with 'classical' two-component reactions. The very high potential for variability, diversity and complexity of MCRs additionally generates an extremely diverse range of products, thus bringing us closer to the aim of being able to produce tailor-made and extremely low-priced materials, drugs and libraries.Keywords: multicomponent reaction; MCR; post condensation modification PCM; post condensation cyclisation PCC; MFCR; multifunction catalysis; variability; diversity; complexity; efficiency of synthesis. PrologueThe high discrepancy between traditional feasibility mania and rational efficiency assessment in chemical synthesis became immediately apparent to the author while working on his thesis and during everyday laboratory life. On the one hand, classic peptide synthesis with an inefficient, extremely high number of synthesis steps and on the other hand, elegant multicomponent reactions that can make such efforts unnecessary. This double strategy in chemical synthesis has given the author cause to reflect (Picture 2) on how to close this gap using a consistent procedure. Picture 2. Problem in chemical syntheses relating to terms of producibility, ecology and economy.

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Multiple Multicomponent Reactions with Isocyanides

Cited by 23 publications

References 83 publications

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

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Multiple Multicomponent Reactions with Isocyanides

Cited by 23 publications

References 83 publications

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Dual side chain control in the synthesis of novel sequence-defined oligomers through the Ugi four-component reaction

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)&mdash;The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules

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Synergy Effects in the Chemical Synthesis and Extensions of Multicomponent Reactions (MCRs)—The Low Energy Way to Ultra-Short Syntheses of Tailor-Made Molecules