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Reactivity Umpolung of Amides in Organic Synthesis

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2023)

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Organobase-Catalyzed Umpolung of Amides: The Generation and Transfer of Carbamoyl Anion

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Summary: A novel organobase-catalyzed umpolung reaction of amides was reported, providing an efficient method for generating and transferring carbamoyl anions while avoiding the disadvantages of carbamoyl metal. Mechanistic analysis revealed that the reaction proceeds through polarity inversion of amide, and a wide range of carbamoyl anions can be used. Additionally, the reaction showed good yields with a variety of substrates.

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New Strategies for the Functionalization of Carbonyl Derivatives via α-Umpolung: From Enolates to Enolonium Ions

Philipp Spiess et al.

Summary: Umpolung is a term describing the reversal of innate polarity, which has become an important tool in synthetic organic chemistry. In this Account, the authors provide an overview of established methods and summarize their findings in the rapidly developing field of umpolung of carbonyl derivatives. They focus on the alpha-umpolung of amides enabled by electrophilic activation and the enolonium chemistry of ketones enabled by hypervalent iodine reagents. The authors discuss the challenges and achievements of these reactions, as well as mechanistic aspects. Rating: 8/10.

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ASIAN JOURNAL OF ORGANIC CHEMISTRY (2023)

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Recent Development in the Catalytic Applications of Pd-NHC (NHC=N-Heterocyclic Carbene) Compounds in Amide C-N Activation Reactions

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Summary: Summarizing the structure-activity relationship of catalysts with different ligand skeletons, we analyze the current bottlenecks encountered in Pd-NHC-catalyzed amide C-N activation reactions and envision the future development of this field.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2023)

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Summary: We report a new method for preparing chiral α-amino amides by directly aminating amides using chiral sulfinamides. This method involves a [2,3]-sigmatropic rearrangement of a crucial sulfonium intermediate. Quantum chemical calculations provide predictive insights into the important E/Z selectivity of the amino-vinyloxy-sulfonium species.

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Summary: Reactivity umpolung, an important concept in organic chemistry, has mainly focused on aldehydes, with little knowledge about the umpolung of amide carbonyl group. In this report, we present a method to achieve the umpolung reactivity of tertiary amides through efficient reductive stannylation catalyzed by Ir/silane and facile Sn-Li exchange. By utilizing this umpolung reactivity, the drug Fluoxetine was successfully derivatized to 12 different analogues via reactions with various electrophiles, and four biologically active molecules were succinctly prepared. This newly discovered umpolung reactivity of tertiary amides is expected to have applications in synthesizing complex amines from amides.

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Summary: Compared to ketones and carboxylic esters, amides have traditionally been considered as less reactive members of the carbonyl family. However, recent research has shown that selective activation of amides under mild conditions is possible. This Minireview highlights the latest advances in this field, showcasing new strategies and breakthroughs in amide activation.

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General Synthesis of Fully Substituted 4-Aminooxazoles from Amides and 1,4,2-Dioxazol-5-ones Based on Amide Activation and Umpolung Process

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Summary: A general and efficient synthesis of fully substituted 4-aminodixazoles was developed using amide activation and umpolung reaction strategies. 1,4,2-dioxazol-5-ones were introduced as a rare type of umpolung reagent with a nucleophilic N-atom, allowing smooth reaction under convenient conditions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Catalytic Generation of Carbanions through Carbonyl Umpolung

Shun Wang et al.

Summary: The article summarizes recent progress in the generation of alkyl carbanions through catalytic carbonyl Umpolung, discussing two different catalytic approaches and their reaction scope, mechanistic insights, synthetic applications, and potential future developments.

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Carbonyl umpolung as an organometallic reagent surrogate

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