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Mitsunobu reaction

About: Mitsunobu reaction is a(n) research topic. Over the lifetime, 1887 publication(s) have been published within this topic receiving 38990 citation(s).
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Journal ArticleDOI
TL;DR: A novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported, and the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1, 3-dipoles entering the reaction.
Abstract: The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]-triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (>95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction.

6,918 citations


Journal ArticleDOI
12 May 1981-Synthesis
Abstract: The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.

3,136 citations


Journal ArticleDOI
Abstract: 2- and 4-Nitrobenzenesulfonamides, readily prepared from primary amines, undergo smooth alkylation by Mitsunobu reaction or by conventional methods to give N-alkylated sulfonamides in near quantitative yields. These sulfonamides could be deprotected readily via Meisenheimer complexes upon treatment with thiolates in DMF at room temperature, giving secondary amines in high yields.

759 citations


Journal ArticleDOI
David L. Hughes1
Abstract: (1996). PROGRESS IN THE MITSUNOBU REACTION. A REVIEW. Organic Preparations and Procedures International: Vol. 28, No. 2, pp. 127-164.

364 citations


Journal ArticleDOI
Abstract: A practical modification of the Mitsunobu protocol for effecting stereochemical inversions of alcohols has been discovered in which use of p-nitrobenzoic acid as the nucleophilic partner results in significantly improved yields with relatively hindered substrates.

317 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202124
202032
201934
201830
201733
201649

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Topic's top 5 most impactful authors

Tokumi Maruyama

10 papers, 40 citations

Joon Hee Hong

9 papers, 18 citations

Shigetada Kozai

9 papers, 34 citations

Ian D. Jenkins

8 papers, 165 citations

Piet Herdewijn

7 papers, 94 citations