Journal ArticleDOI
Progress in the mitsunobu reaction. a review
TLDR
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.About:
This article is published in Organic Preparations and Procedures International.The article was published on 1996-04-01. It has received 373 citations till now. The article focuses on the topics: Mitsunobu reaction.read more
Citations
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Journal ArticleDOI
Carbon nucleophiles in the Mitsunobu reaction. Mono- and dialkylation of bis(2,2,2-trifluoroethyl) malonates.
TL;DR: B bis( 2,2,2-trifluoroethyl) malonate readily undergoes dehydrative alkylation with primary alcohols, and using only a slight excess of malonates gives monoalkylated product in good yield.
Journal ArticleDOI
Fluorous, chromatography-free Mitsunobu reaction.
TL;DR: A simple, chromatography-free isolation protocol with excellent yields in the presence of Ph3P and DIAD in THF at room temperature (fluorous Mitsunobu).
Journal ArticleDOI
Structurally diverse penta- and hexacoordinate phosphorus compounds from the reaction of diethyl or diisopropyl azodicarboxylates with phosphorus(III) compounds
TL;DR: In this paper, the structural preference of spirocyclic penta- and tricyclic hexacoordinate (amino)oxyphosphoranes has been examined in an effort to delineate the structural preferences in spirocycleic pentanaphoric compounds.
Journal ArticleDOI
Monomer-on-monomer (MoM) Mitsunobu reaction: facile purification utilizing surface-initiated sequestration.
Pradip K. Maity,Alan Rolfe,Thiwanka Samarakoon,Saqib Faisal,Ryan D. Kurtz,Toby R. Long,Alexander Schätz,Daniel L. Flynn,Robert N. Grass,Wendelin J. Stark,Oliver Reiser,Paul R. Hanson +11 more
TL;DR: A monomer-on-monomer (MoM) Mitsunobu reaction utilizing norbornenyl-tagged (Nb- tagged) reagents is reported, whereby purification was rapidly achieved by employing ring-opening metathesis polymerization.
Journal ArticleDOI
Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides.
TL;DR: The total synthesis of phytuberin, a phytoalexin of the Solanum genus, from (-)-alpha-santonin is reported, with an unprecedented 4-exo selenocyclization of a homoallylic alcohol.
References
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Journal ArticleDOI
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
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.
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Conformational analysis—CI
TL;DR: In this paper, it was concluded that the gauche-butane interaction has been incorrectly interpreted as to origin, and that the relationship between methyl groups is not the cause of the relative instability of gauche conformations.
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Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
Oyo Mitsunobu,Masaaki Yamada +1 more
TL;DR: In this article, the reaction of carboxylic acid with triphenyl phosphine and diethyl azodicarboxylate in the presence of an alcohol has been studied.
Journal ArticleDOI
Efficacious modification of the mitsunobu reaction for inversions of sterically hindered secondary alcohols
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.
Journal ArticleDOI
Direct conversion of activated alcohols to azides using diphenyl phosphorazidate. A practical alternative to mitsunobu conditions
TL;DR: In this article, 14 alcohols were converted to their corresponding azides with inversion of configuration using diphenyl phosphorazidate and DBU, and the resulting azides were converted into azides.
Related Papers (5)
The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts
Oyo Mitsunobu,Masaaki Yamada +1 more