scispace - formally typeset
Search or ask a question
Topic

Mitsunobu reaction

About: Mitsunobu reaction is a research topic. Over the lifetime, 1887 publications have been published within this topic receiving 38990 citations.


Papers
More filters
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.

7,397 citations

Journal ArticleDOI
TL;DR: In this article, a 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.
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.

3,209 citations

Journal ArticleDOI
TL;DR: In this paper, 2-and 4-nitrobenzenesulfonamides are obtained from primary amines and undergo smooth alkylation by Mitsunobu reaction or by conventional methods to give N-alkylated sulfonamide in near quantitative yields.

784 citations

Journal ArticleDOI
David L. Hughes1
TL;DR: A review of progress in the MITSUNOBU this article reaction can be found in this article, with a focus on the MIT SUNOBU reaction and a review of the progress.

373 citations

Journal ArticleDOI
TL;DR: In this article, a 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.

320 citations


Network Information
Related Topics (5)
Aryl
95.6K papers, 1.3M citations
94% related
Enantioselective synthesis
58.1K papers, 1.6M citations
93% related
Cycloaddition
39.9K papers, 728.7K citations
93% related
Moiety
40K papers, 615K citations
91% related
Alkyl
223.5K papers, 2M citations
90% related
Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202318
202215
202124
202032
201934
201830