NMR and X-ray crystallographic studies of axial and equatorial 2-ethoxy-2-oxo-1,4,2-oxazaphosphinane

Linzaga-Elizalde, Irma; Escalante, Jaime; Muñoz, Miguel Á.; Juaristi, Eusebio

doi:10.1016/s0040-4020(02)01152-3

Cited by 18 publications

(7 citation statements)

References 24 publications

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“…Treatment of carbinol (S)-325 with KH in THF solution afforded cyclized products 326 in good yield (Scheme 103). 158 Also, compound 307 was treated with trimethyl phosphite and formaldehyde to give N-(phosphonomethyl)oxazolidine 327. Treatment of 327 with phenyl magnesium bromide and in the presence of TiCl 4 gave directly the expected 326 (R=Me) but in low yield (Scheme 103).…”

Section: Scheme 100mentioning

confidence: 99%

Synthetic methods of cyclic α-aminophosphonic acids and their esters

Ali¹

2013

Arkivoc

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Section: Scheme 100mentioning

confidence: 99%

Synthetic methods of cyclic α-aminophosphonic acids and their esters

Ali¹

2013

Arkivoc

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“…118 A convenient synthetic approach to highly reactive N-(arylsulfonyl)trichloro-and trifluoroacetimidoyl chlorides (244) by reacting the corresponding N-acylsulfonamides with PCl 5 has been elaborated. The interaction of (244) with phosphites proceeds through different pathways depending on the substituents in the reagents, and leads to compounds (245), (246), (247) (249) and (250) afforded a single diastereoisomer of the corresponding acetates (251) in high enantiomeric excess (>98%) (Figure 46). 120 Diastereoselective synthesis of b-substituted a-hydroxyphosphinates (252) and (253) by hydroxyphosphinylation of a-silyloxy aldehydes (254) and aamino aldehydes (255) with ethyl allylphosphinate (256), catalysed with lithium phenoxide, has been reported ( Figure 47).…”

Section: Halogenoalkyl and Halogenocycloalkyl Acidsmentioning

confidence: 99%

“…In extracellular ELISA-based assays (521), exhibits potent Grb2 SH2 domain binding affinity (IC 50 ¼ 8nM) (Figure 104) (Figure 105). 246 1,3,2-Dioxaphosphorinane derivatives containing a substituent with different steric arrangement at the C5 position (529)-(532) have been prepared. 240 The enantiomers of a novel unsaturated phosphonocholine antitumor ether lipid (523) were synthesized and found to have differential antiproliferative effects against epithelial cancer cell lines.…”

Section: Figure 93mentioning

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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“…It has been shown recently that aminomethanephosphonic acid derivatives of chiral 2-aminoethanol substrates give rise to six-membered heterocyclic 1,4,2-oxazaphosphinanes 2 that are interesting starting materials for the preparation of enantiopure phosphonic acid analogues of ␣-amino acids [7][8][9]. Herein, we describe procedures for the preparation of a series of four (3-hydroxypropylamino)(aryl)methylphosphonates 3a-3d, a seven-membered 1,4,2-oxazaphosphepane 4d, diethyl(1,3-oxazinan-3-ylmethyl)phosphonate 5, and {[(3-hydroxypropyl)amino]methyl}phosphonic acid 6.…”

Section: Introductionmentioning

confidence: 99%

Linear and cyclic aminomethanephosphonic acid esters derived from benzaldehyde derivatives, 3-aminopropanol, and diethyl phosphite

et al. 2006

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A series of four diethyl {[(3-hydroxy-propyl)amino](aryl)methyl}phosphonates have been prepared and characterized. In one case, the phosphonate was transformed to a seven-membered 1,4,2-oxazaphosphepane heterocycle through a one-pot intramolecular esterification. The analogous reaction with formaldehyde gave the six-membered diethyl (1,3-oxazinan-3-ylmethyl)phosphonate, which could be transformed in a posterior reaction to the corresponding aminomethanephosphonic acid.

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NMR and X-ray crystallographic studies of axial and equatorial 2-ethoxy-2-oxo-1,4,2-oxazaphosphinane

Cited by 18 publications

References 24 publications

Synthetic methods of cyclic α-aminophosphonic acids and their esters

Synthetic methods of cyclic α-aminophosphonic acids and their esters

Organophosphorus Chemistry

Linear and cyclic aminomethanephosphonic acid esters derived from benzaldehyde derivatives, 3-aminopropanol, and diethyl phosphite

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