A New Synthesis of α-Ketophosphonates

Afarinkia, K.; Faller, A.; Twist, Andrew

doi:10.1055/s-2003-37341

Cited by 10 publications

(2 citation statements)

References 4 publications

(8 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Distinct from acetals 33 [23,132], the two sulfur atoms of thioacetals 113 , 114 stabilize well the neighboring carbanion [23], therefore the α-hydrogen atom in the thioacetal group is readily removed under the action of strong bases [23,132] in both dialkyl (dialkythiomethyl)phosphonates 113 , 114 [135] and diphenyl(dialkythiomethyl)phosphine oxides 121 , 122 [113]. Further, the carbanions are readily alkylated with alkyl halides [113,135]. For example, dialkyl ([1,3]-dithian-2-yl)phosphonates 114 in this reaction produce dialkyl [(2-alkyl-[1,3]-dithian)-2-yl]phosphonates 214 , and their oxidative decomposition may result in α-phosphorylated carbonyl compounds 215 (Scheme 64).…”

Section: General Chemical Properties Of Phosphorylated Formaldehydmentioning

confidence: 99%

Chemistry of Phosphorylated Formaldehyde Derivatives. Part I

Morgalyuk

2014

Molecules

View full text Add to dashboard Cite

Abstract:The underinvestigated derivatives of unstable phosphorylated formaldehyde acetals and some of the structurally related compounds, such as thioacetals, aminonitriles, aminomethylphosphinoyl compounds, are considered. Separately considered are halogen aminals of phosphorylated formaldehyde, acetals of phosphorylated formaldehyde of H-phosphinate-type and a phosphorylated gem-diol of formaldehyde. Synthetic methods, chemical properties and examples of practical applications are given.

show abstract

Section: General Chemical Properties Of Phosphorylated Formaldehydmentioning

confidence: 99%

Chemistry of Phosphorylated Formaldehyde Derivatives. Part I

Morgalyuk

2014

Molecules

View full text Add to dashboard Cite

show abstract

“…This phosphonate (282) was next enzymatically converted into (3R,4R)-3,4,5-trihydroxyphosphonic acid (284), an isosteric analogue of 2-C-methyl-D-erythritol-4-phosphate (Scheme 72). 133 Acylation of methythio-1-lithiomethylphosphonate (299) with 2 0 -and 3 0substituted benzoyl chlorides (300) constitutes an efficient synthesis of diethyl 1-methylthio-2-oxo-2-phenylethylphosphonates (301) (Scheme 76). Kinetic resolution by specially selected reaction sequences led to phosphocarnitine (291), phosphogabob (292) and phosphomycin (293) respectively (Scheme 73).…”

Section: Halogenoalkyl and Halogenocycloalkyl Acidsmentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

View full text Add to dashboard Cite

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-

show abstract