ChemInform Abstract: 3‐Furanylphosphonates (III).

Malenko, D. M.; Simurova, Natalia; Randina, L. V.; Sinitsa, A. D.

doi:10.1002/chin.199014226

Cited by 3 publications

(3 citation statements)

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“…22,26,27,29 A large number of investigations have led to proposing four types of mechanisms involving an initial attack of the phosphorus on: the halogen, 31 the carbonyl oxygen, 32 the acarbon bound to the halogen 33 or on the carbonyl carbon. 34,35 Formation of the vinyl phosphate, epoxyphosphonate and phosphate halohydrin is believed to result from attack by the phosphorus at the carbonyl carbon. Formation of the b-oxophosphonate results from attack at the a-halo carbon.…”

Section: Methodsmentioning

confidence: 99%

The Syntheses and Properties of 1,2-Epoxyalkylphosphonates

Iorga¹,

Eymery²,

Savignac³

1999

Synthesis

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This review article deals with the methods of preparation of dialkyl 1,2-epoxyalkylphosphonates as well as synthetically useful reactions of this class of compounds. Four main routes to 1,2-epoxyalkylphosphonates are described, in which new developments adapted to each processes are given, including the choice of the leaving group, new cyclisation methods and stereocontrol induction. Thermal and acid-catalyzed rearrangements are also covered, and the use of the oxirane ring by nucleophilic opening is highlighted. Particular emphasis is placed on the synthetic approaches to antibiotic fosfomycin.

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Section: Methodsmentioning

confidence: 99%

The Syntheses and Properties of 1,2-Epoxyalkylphosphonates

Iorga¹,

Eymery²,

Savignac³

1999

Synthesis

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“…Later, 3‐ethylidene acetylacetone 55 was found to react with dimethyl phosphorisocyanatidite 56 to give product 54 again (Scheme , method B) . 3‐Ethylidene acetylacetone 55 also gave rise to oxaphospholenes after reaction of its enolate with diethyl chlorophosphite, followed by a cyclization step (Scheme , method C) . In this way, oxaphospholenes with a fluorine‐containing ester chain could be prepared as well when fluorinated dialkyl phosphite was used …”

Section: Synthetic Routes Towards Oxaphospholenes and Benzoxaphospholmentioning

confidence: 99%

Fifty Years of (Benz)oxaphospholene Chemistry

Berton

Heugebaert

Virieux

et al. 2017

Chemistry A European J

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The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then,t he structuralv ariety of reported (benz)oxaphospholenesh as steadily increased. Organophosphorusc ompounds have caught the interesto fs ynthetic chemists for ac ouple of decades now because of their interesting biological properties. Oxaphospholenes,i n particular,c ould serve as carbohydrate mimetics, and benzoxaphospholenes have been reported to possess bactericidal, insecticidal, herbicidal, and fungistatical properties. Transesterification reactions and addition of phosphorus nucleophiles to carbonylc ompoundsw ere reaction types that led to the production of the first (benz)oxaphospholenes.When it was discovered that allenylphosphonates could easily be obtainedf rom propargyl alcohols and dialkylh alophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in ah uge boom in the amounto fr eports on oxaphospholene synthesis. To this day,t his methodi ss till frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also provent heir potentialf or the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry,g enerating (benz)oxaphospholenes from a wide variety of simple substrates. Ac ouple of miscellaneous methods are summarized at the end of the Review.[a] J.

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“…50,51,53 Reactions of phosphorochloridites and crotonaldehyde in the presence of triethylamine occur with proton abstraction from the methyl group at the double bond and the formation of butadienyl phosphites. 61 We believe that the initial attack of phosphorochloridite on the oxygen atom of the carbonyl group is followed by proton abstraction from the methyl group.…”

Section: + Pcl3 Pclmentioning

confidence: 99%