Stereoselective synthesis of α-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, via electrophilic fluorination of lithiated bis-lactim ethersElectronic supplementary information (ESI) available: experimental data. See http://www.rsc.org/suppdata/cc/b2/b204093j/

Ruiz, Marı́a; Ojea, Vicente; Quintela, José M.; Guillin, Juan J.

doi:10.1039/b204093j

Cited by 21 publications

(8 citation statements)

References 16 publications

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“…α-Monofluorinated phosphonate mimics of phosphoserine and phosphothreonine were synthesized via electrophilic fluorination of Schöllkopf's bislactim ethers derived from cyclo[ l -(2-amino-4-phosphonobutanoic acid)- d -valine]. However, the chiral auxiliary only produced moderate to no diastereoselectivity in the fluorination with NFSI (Scheme ) 16 …”

Section: 11 Diastereoselective Fluorinationmentioning

confidence: 99%

Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

2004

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Section: 11 Diastereoselective Fluorinationmentioning

confidence: 99%

Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

2004

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“…Ruiz et al exploited Schöllkopf's bislactim ethers 49 as the chiral starting materials, which were fluorinated with NFSI in the presence of LDA to produce the diastereomeric phosphonates 50 . The best result did not exceed 50% de for 66% yield (Scheme ) 18 …”

Section: 2 Electrophilic Fluorination Of Phosphonate Carbanionsmentioning

confidence: 96%

Fluorinated Phosphonates: Synthesis and Biomedical Application

Romanenko¹,

Kukhar²

2006

Chem. Rev.

348

185

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“…145 Condensation of the new pentacoordinate oxaphospholene (326) with azadicarboxylate, followed by reduction of the resultant ketone (327) produce cis-and/or trans-oxazolidones (328), potential precursors to phosphonate analogues of sphingomyelin, sphingosine 1-phosphate and ceramide 1-phosphate (Scheme 88). 155 A novel preparation of racemic and enantiopure forms of phosphocarnitine (348) from easily available 3-chloro-2-oxopropylphosphonate (349) has been accomplished. 147 The reaction of oxazolines (331) derived from L-serine with diethylphosphite leads to a mixture of racemic aand b-phosphono alanines (332) and (333).…”

Section: Halogenoalkyl and Halogenocycloalkyl Acidsmentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

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Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series highlights and details some of the novel methods that are advancing the field of organophosphorus chemistry.The Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors. More specifically, the Thematic Series spans new methods in C-P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to phosphinoyl-indoles and phosphinoyl-isocoumarins and new chemistries of H-phosphonates. The Thematic Series also details work on new metathesis-based reactions of vinyl phosphonates and phosphate tethers, novel phosphorus-based ligands in asymmetric catalysis, novel rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagents, the Atherton-Todd reaction, cyclic phosphonium ionic liquids with distinct properties, photo-removable phosphate protecting groups, new methods of C-H functionalization using phosphoryl-related directing groups, the exciting chemistry of substituted phosphanylidenecarbenes and phosphoryl azides, and bisphosphonate ethers as promising inhibitors of geranylgeranyl diphosphate synthase (GGDPS).The articles and reviews capture the emerging potential of organophosphorus compounds and exciting opportunities in the field, and hopefully, will inspire and motivate investigators in the field to investigate new chemistry in this area. Taken collectively, organophosphorus chemistry embodies a broad, vibrant and continual growing scientific area with this Thematic Series highlighting recent advances in the field. We are grateful and indebted to the authors for their hard work and exciting contri-

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Cited by 21 publications

References 16 publications

Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

Fluorinated Phosphonates: Synthesis and Biomedical Application

Organophosphorus Chemistry

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