The Experts below are selected from a list of 18 Experts worldwide ranked by ideXlab platform
Christopher Hulme - One of the best experts on this subject based on the ideXlab platform.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
Organic Letters, 2018Co-Authors: Christopher Foley, Arthur Y. Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
2018Co-Authors: Christopher Foley, Arthur Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps
Christopher Foley - One of the best experts on this subject based on the ideXlab platform.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
Organic Letters, 2018Co-Authors: Christopher Foley, Arthur Y. Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
2018Co-Authors: Christopher Foley, Arthur Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps
Arthur Y. Shaw - One of the best experts on this subject based on the ideXlab platform.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
Organic Letters, 2018Co-Authors: Christopher Foley, Arthur Y. Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps.
Arthur Shaw - One of the best experts on this subject based on the ideXlab platform.
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Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
2018Co-Authors: Christopher Foley, Arthur Shaw, Christopher HulmeAbstract:Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction–oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C–N Oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley Oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps
Jonathan S Lindsey - One of the best experts on this subject based on the ideXlab platform.
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Riley Oxidation of heterocyclic intermediates on paths to hydroporphyrins a review
Molecules, 2020Co-Authors: Pengzhi Wang, Jonathan S LindseyAbstract:Riley Oxidation of advanced heterocyclic intermediates (dihydrodipyrrins and tetrahydrodipyrrins) is pivotal in routes to synthetic hydroporphyrins including chlorins, bacteriochlorins, and model (bacterio)chlorophylls. Such macrocycles find wide use in studies ranging from energy sciences to photomedicine. The key transformation (-CH3 → -CHO) is often inefficient, however, thereby crimping the synthesis of hydroporphyrins. The first part of the review summarizes 12 representative conditions for Riley Oxidation across diverse (non-hydrodipyrrin) substrates. An interlude summarizes the proposed mechanisms and provides context concerning the nature of various selenium species other than SeO2. The second part of the review comprehensively reports the conditions and results upon Riley Oxidation of 45 1-methyltetrahydrodipyrrins and 1-methyldihydrodipyrrins. A comparison of the results provides insights into the tolerable structural features for Riley Oxidation of hydrodipyrrins. In general, Riley Oxidation of dihydrodipyrrins has a broad scope toward substituents, but proceeds in only modest yield. Too few tetrahydrodipyrrins have been examined to draw conclusions concerning scope. New reaction conditions or approaches will be required to achieve high yields for this critical transformation in the synthesis of hydroporphyrins.
