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
More filters
Journal ArticleDOI
A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone(DDQ)/n-Bu4NN3 system
TL;DR: Alcohols, thiols, and silyl ethers are converted into alkyl azides in good yields by treatment with PPh3/DDQ/n-Bu4NN3 in CH2Cl2 at room temperature.
Journal ArticleDOI
Synthesis of tetrahydrobenzoxazepine acetals with electron-withdrawing groups on the nitrogen atom. Novel scaffolds endowed with anticancer activity against breast cancer cells
Mónica Díaz-Gavilán,Fernando Rodríguez-Serrano,José A. Gómez-Vidal,Juan A. Marchal,Antonia Aránega,Miguel A. Gallo,Antonio Espinosa,Joaquín M. Campos +7 more
TL;DR: In particular, the presence of a trifluoroacetyl moiety on the nitrogen atom leads to amides displaying interesting in vitro antitumour activities as mentioned in this paper, which can be used as scaffolds for the preparation of new O, N -acetals as anticancer agents, unexpectedly proved to show antiproliferative activity against the MCF-7 breast cancer cell line.
Journal ArticleDOI
Synthesis and SAR of 1,2,3,4-tetrahydroisoquinolin-1-ones as novel G-protein-coupled receptor 40 (GPR40) antagonists.
Paul S. Humphries,John William Benbow,Paul D. Bonin,David D. Boyer,Shawn D. Doran,Richard K. Frisbie,David W. Piotrowski,Gayatri Balan,Bruce M. Bechle,Edward L. Conn,Kenneth J. DiRico,Robert M. Oliver,Walter C. Soeller,James A. Southers,Xiaojing Yang +14 more
TL;DR: The development of a series of novel 1,2,3,4-tetrahydroisoquinolin-1-ones as antagonists of G protein-coupled receptor 40 (GPR40) is described and led to the identification of 15i, whose rat oral pharmacokinetic data is reported.
Journal ArticleDOI
The Hendrickson reagent and the Mitsunobu reaction: a mechanistic study.
TL;DR: The mechanism of the Mitsunobu reaction is discussed in the light of the dramatic salt effect on both the rate and outcome of the reaction and the possible involvement of ion pair clustering.
Journal ArticleDOI
Sterically biased 3,3-sigmatropic rearrangement of azides: efficient preparation of nonracemic alpha-amino acids and heterocycles.
TL;DR: Homochiral alpha-amino acids, heterocycles, and carbocycles are efficiently constructed via a short sequence of reactions starting from the chiral auxiliary p-menthane-3-carboxaldehyde that procures enantiomerically enriched allylic azides.
References
More filters
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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