Aliphatic Diazo Compounds, Nitrones, and Structurally Analogous Compounds. Systems Capable of Undergoing 1,3-Additions.

Smith, Lee Irvin

doi:10.1021/cr60075a001

Cited by 138 publications

(36 citation statements)

References 130 publications

(166 reference statements)

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“…The synthesis of triazoles by thermal 1,3‐dipolar cycloaddition of alkynes and azides was first described by Michael et al . and later studied systematically by Huisgen .…”

Section: Introductionmentioning

confidence: 99%

1,5‐Disubstituted 1,2,3‐Triazole‐Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

Kracker

Góra

Krzciuk-Gula

et al. 2017

Chemistry A European J

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Peptidotriazolamers are hybrid foldamers combining features of peptides and triazolamers-repetitive peptidomimetic structures with triazoles replacing peptide bonds. We report on the synthesis of a new class of peptidomimetics, containing 1,5-disubstituted 1,2,3-triazoles in an alternating fashion with amide bonds and the analysis of their conformation in solid state and solution. Homo- or heterochiral peptidotriazolamers were obtained from enantiomerically pure propargylamines with stereogenic centers in the propargylic position and α-azido esters by ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) under microwave conditions in high yields. With such building blocks the peptidotriazolamers are readily available by solution phase synthesis. While the conformation of the homochiral peptidotriazolamer Boc-Ala[5Tz]Phe-Val[5Tz]Ala-Leu[5Tz]Val-OBzl resembles that of a β VIa1 turn, the heterochiral peptidotriazolamer Boc-d-Ala[5Tz]Phe-d-Val[5Tz]Ala-d-Leu[5Tz]Val-OBzl adopts a polyproline-like repetitive structure.

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“…The synthesis of triazoles by thermal 1,3‐dipolar cycloaddition of alkynes and azides was first described by Michael et al . and later studied systematically by Huisgen .…”

Section: Introductionmentioning

confidence: 99%

1,5‐Disubstituted 1,2,3‐Triazole‐Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

Kracker

Góra

Krzciuk-Gula

et al. 2017

Chemistry A European J

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“…Among the various transformations using diazocompounds, Brønsted acid catalysis is a well‐established process for the generation of diazonium cations as electrophiles. For example, O−H insertion reactions, esterifications of carboxylic acids, and nucleophilic substitution reactions are representative transformations for the effective use of diazonium cations generated from the diazo functionality and Brønsted acid catalyst.…”

Section: Introductionmentioning

confidence: 99%

Merging Brønsted Acid and Hydrogen‐Bonding Catalysis: Metal‐Free Dearomatization of Phenols via ipso‐Friedel‐Crafts Alkylation to Produce Functionalized Spirolactams

et al. 2018

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Intramolecular dearomative cyclization of phenols with a-diazoamide units for synthesizing functionalized spirolactams was developed by merging Brønsted acid and hydrogen-bonding catalysis as an advantageous alternative to transition metal catalysis. This metal carbenoid-free strategy enables high chemoselectivity by suppressing potentially competing CÀH insertion reactions and a Bü chner reaction. Preliminary mechanistic studies were performed to elucidate the positive effect of the combined use of the catalysts, and extension to an asymmetric reaction was achieved.

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“…The simplicity of the reaction protocol, combined with the ease of removal of only dinitrogen as a coproduct, made for a transformation that was often reliable, chemoselective, and high yielding. [2] As a result, complex mixtures of natural product extracts were routinely treated with diazomethane to convert carboxylic acid components into their more lipophilic ester derivatives. Moreover, the simplicity of the reaction mechanism lent itself to adaptation by students of organic chemistry for many years: for example, proton transfer to the diazomethane carbon, [3] followed by collapse of the ion pair to form the ester and dinitrogen.…”

Section: Introductionmentioning

confidence: 99%

To Protonate or Alkylate? Stereoselective Brønsted Acid Catalysis of CC Bond Formation Using Diazoalkanes

2010

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A new means to activate diazoalkanes has been discovered and applied broadly over the past few years. Brønsted acids, both achiral and chiral, have been used to promote the formation of carbon-carbon and carbon-heteroatom bonds with a growing number of diazoalkane derivatives. Aside from their straightforward ability to build structural and stereochemical complexity in innovative new ways, these transformations are remarkable owing to their ability to skirt competitive diazo protonation--a reaction that has long been used to prepare esters efficiently and cleanly from carboxylic acids. In cases where achiral Brønsted acids are used, high diastereoselection can be achieved. Meanwhile, chiral Brønsted acids can deliver products with both high diastereo- and enantioselectivity. More recently, systems have emerged that combine Brønsted acids and either Lewis acids or transition metals to promote carbon-carbon bond formation from diazoalkanes.

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Aliphatic Diazo Compounds, Nitrones, and Structurally Analogous Compounds. Systems Capable of Undergoing 1,3-Additions.

Cited by 138 publications

References 130 publications

1,5‐Disubstituted 1,2,3‐Triazole‐Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

1,5‐Disubstituted 1,2,3‐Triazole‐Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics

Merging Brønsted Acid and Hydrogen‐Bonding Catalysis: Metal‐Free Dearomatization of Phenols via ipso‐Friedel‐Crafts Alkylation to Produce Functionalized Spirolactams

To Protonate or Alkylate? Stereoselective Brønsted Acid Catalysis of CC Bond Formation Using Diazoalkanes

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