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Journal ArticleDOI

Progress in the mitsunobu reaction. a review

David L. Hughes
- 01 Apr 1996 - 
- Vol. 28, Iss: 2, pp 127-164
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.
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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.

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Citations
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Di-p-nitrobenzyl azodicarboxylate (DNAD): an alternative azo-reagent for the Mitsunobu reaction

TL;DR: In this paper, the hydrazine produced from DNAD is semisoluble in some solvents such as THF and CH2Cl2, which makes it separated easily from the reaction mixture just via filtration.
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The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review)

TL;DR: In this paper, the design of nitrogen-containing heterocyclic systems involving the formation of C-N bonds under the conditions of the Mitsunobu reaction is discussed.
Journal ArticleDOI

Enantio- and diastereocontrolled synthesis of (−)-19(S)-acetoxy-N1-acetyl-20-epitubifolidine

TL;DR: An enantiocontrolled route to the 19-oxygenated pentacyclic Strychnos alkaloids has been demonstrated by the stereoselective synthesis of (−)-19(S )-acetoxy- N 1 -acetyl-20-epitubifolidine as discussed by the authors.
Journal ArticleDOI

Total synthesis of antitumor agents, (+)-goniopypyrone and (+)-7-epi-goniofufurone

TL;DR: In this paper, the synthesis of enantiopure (+)-7-epi-goniofufurone, 1 and (+)-goniopypyrone 2 has been achieved from C-4 carbon chain chiron 3, readily available from (R)-mandelic acid.
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The reaction of acyl cyanides with “Huisgen zwitterion”: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms

TL;DR: A novel rearrangement involving ester group migration was found in the reaction of acyl cyanides and Huisgen zwitterions, affording hydrazone derivatives at higher temperature (90 degrees C) and azine derivatives at lower temperature (20 degrees C), respectively.
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

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.
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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.
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