Reactions of trivalent phosphorus compounds with azides containing a mobile H-atom

Gololobov, Yu. G.; Gusar, N. I.; Chaus, M. P.

doi:10.1016/s0040-4020(01)96459-2

Cited by 35 publications

(11 citation statements)

References 7 publications

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“…Amides should be even less reactive, and had in fact been found to be inert under the conditions described previously. The few examples of amides undergoing aza‐Wittig reactions employed highly activated (i.e., electron‐poor) substrates or harsh conditions 17c,17g,18…”

Section: Resultsmentioning

confidence: 99%

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Unified Azoline and Azole Syntheses by Optimized Aza‐Wittig Chemistry

et al. 2013

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Intramolecular aza‐Wittig ring closures were applied to synthesize thiazolines, oxazolines, and imidazolines from β‐azido thioester, ester, and amide precursors. The cyclization precursors were obtained from amino acid derivatives. Optimized conditions for diazo transfer with a fast rate and racemization suppression, (thio)esterification, and amide coupling reactions are described. The ring closure reaction can be executed with PPh3 under neutral conditions and was found to be highly chemoselective for five‐membered rings. If amide groups were activated with tosyl groups, smooth intramolecular ring closure of iminophosphoranes furnished enantiopure imidazoline products with position‐specific tosyl protection. This aza‐Wittig‐based azoline synthesis was then extended to double azoline ring closures to furnish catenated azoline building blocks common to peptide natural product building blocks and their analogues.

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Section: Resultsmentioning

confidence: 99%

“…Isolated examples of such aza‐Wittig‐driven formation of thiazolines and oxazolines have been reported 16. The synthesis of imidazolines has been reported only for unusually activated systems 17–18. Thereby, accessible substitution patterns are limited or forcing reaction conditions had to be applied 18…”

Section: Introductionmentioning

confidence: 99%

Unified Azoline and Azole Syntheses by Optimized Aza‐Wittig Chemistry

et al. 2013

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“…The higher percentage removal of the phosphate ions at lower influent concentration despite reduction in the mass transfer coefficient is due to the availability of active sites which provided enough space for optimum solute molecules adsorption. At lower inlet concentration an extended breakthrough curve was obtained, however, at higher concentrations there were increasing driving force of the solutes toward the adsorbent, more phosphates ions were unadsorbed as a result of saturation of active sites (Gololobov, 1985) 3.5. Analysis of fixed bed models…”

Section: Column Performance Evaluation At Varying Initial Concentrationmentioning

confidence: 95%

Immobilization of maize tassel in polyvinyl alcohol for the removal of phosphoric compounds from surface water near farmland

et al. 2021

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“…Azido acids are often used as precursors to 1,3-azoles and azolines in peptide synthesis. Early examples of this were described by Brossmer in 1981 148 and by Gololobov in 1985, 149 who found that aza-Wittig reactions could be performed intramolecularly on thioamides, carboxyamides and oxyesters to produce thiazolines, imidazolines and oxazolines, respectively. Despite the utility of this reaction, aza-Wittig reactions on esters and amides were not explored further until 2003 when Chen and Forsyth utilized them in their synthesis of apratoxin A (Scheme 40).…”

Section: -Azido Acids In the Synthesis Of Azoles And Azolinesmentioning

confidence: 99%

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

Moreira¹,

Noden²,

Taylor³

2020

Synthesis

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Azido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.1 Introduction2 Synthesis of α-Azido Acids2.1 From α-Amino Acids or Esters2.2 Via α-Substitution2.3 Via Electrophilic Azidation2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters3 Synthesis of β-Azido Acids3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine and AABA4 Azido Acids in Total Synthesis4.1 α-Azido Acids4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain5 Conclusions

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Reactions of trivalent phosphorus compounds with azides containing a mobile H-atom

Cited by 35 publications

References 7 publications

Unified Azoline and Azole Syntheses by Optimized Aza‐Wittig Chemistry

Unified Azoline and Azole Syntheses by Optimized Aza‐Wittig Chemistry

Immobilization of maize tassel in polyvinyl alcohol for the removal of phosphoric compounds from surface water near farmland

Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides

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