Stereoselective synthesis of trifluoromethylated vinyl- and dienylphosphonates with γ-alkoxycarbonyl moiety

Shen, Yanchang; Li, Ping

doi:10.1016/j.jfluchem.2003.10.004

Cited by 3 publications

(4 citation statements)

References 21 publications

(19 reference statements)

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“…Trifluoroacetylated diphosphonate [(EtO) 2 P(O)] 2 C(Me)C(O)CF 3 may be generated from the diphosphoryl-stabilized carbanion salt [(EtO) 2 P(O)] 2 C(Me)Li and trifluoroacetic anhydride. This reagent generated in situ is effective for the stereoselective synthesis of trifluoromethylated vinyl- and dienylphosphonates, which are useful building blocks for the synthesis of biologically active hetero- and carbocyclic compounds. , …”

Section: 11 Simple Fluorine-containing Diphosphonatesmentioning

confidence: 99%

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Fluorinated Phosphonates: Synthesis and Biomedical Application

Romanenko¹,

Kukhar²

2006

Chem. Rev.

343

185

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Section: 11 Simple Fluorine-containing Diphosphonatesmentioning

confidence: 99%

“…This reagent generated in situ is effective for the stereoselective synthesis of trifluoromethylated vinyl-and dienylphosphonates, which are useful building blocks for the synthesis of biologically active hetero-and carbocyclic compounds. 289,290…”

Section: Simple Fluorine-containing Diphosphonatesmentioning

confidence: 99%

Fluorinated Phosphonates: Synthesis and Biomedical Application

Romanenko¹,

Kukhar²

2006

Chem. Rev.

343

185

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“…Compounds (86) were converted into the corresponding methyl or benzyl phosphorothioamides (89) by DBU-assisted treatment with methyl or benzyl alcohol. 58 A highly regio-, diastereo-, and enantioselective desymmetrisation of five-, six-, and seven-membered meso-cyclic allylic bis-diethyl phosphates (104), (105) and (106), was achieved with diethylzinc using catalytic amounts of [Cu(OTf)] 2 , C 6 H 6 and phosphoramidite ligands (107). 48 An oxathiaphospholane approach to one-pot phosphorothioylation of isoprenoid alcohols such as allyl, geranyl, isopentenyl, citronellyl, farnesyl, and phytyl alcohols has also been reported (Scheme 24).…”

Section: Scheme 13mentioning

confidence: 99%

“…102 Palladium acetate catalysed Mizoroki-Heck reaction of arylboronic acids (198) with diethyl vinylphosphonates (199) is an effective synthetic approach to aryl substituted a,b-unsaturated phosphonates (200) of (E) stereochemistry (Scheme 54). 104 Differently substituted 1,3-dienes (204) readily add to vinylidene bis-phosphonate (205) to give the corresponding cyclohex-3-ene-1,1-bis-phosphonates (206). It involves acylation of ethyl-1,1-bisphosphonate (202) with trifluoroacetic anhydride, addition of selected Reformatsky reagents to the resulting 1-trifluoroacetyl-1,1-ethyl bisphosphonates (203) and finally spontaneous Horner-Wadsworth-Emmons (HWE) olefination of the adducts (Scheme 55).…”

Section: Scheme 41mentioning

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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