Search for "phosphonites" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101
Graphical Abstract
Figure 1: Bond lengths and bond angles in oxetane at 140 K [2].
Figure 2: Analogy of 3-substituted oxetanes to carbonyl and gem-dimethyl groups [12].
Figure 3: Use of oxetanes in drug design – selected examples.
Figure 4: Examples of oxetane-containing natural products.
Scheme 1: Synthetic strategies towards construction of the oxetane ring.
Scheme 2: Overview of intramolecular Williamson etherification and competing Grob fragmentation.
Scheme 3: Synthesis of spiro-oxetanes via 1,4-C–H insertion and Williamson etherification.
Scheme 4: Use of phenyl vinyl selenone in the synthesis of spirooxindole oxetanes.
Scheme 5: Synthesis of bicyclic 3,5-anhydrofuranoses via double epoxide opening/etherification.
Scheme 6: Preparation of spirooxetanes by cycloisomerisation via MHAT/RPC.
Scheme 7: Oxetane synthesis via alcohol C–H functionalisation.
Scheme 8: Access to oxetanes 38 from α-acetyloxy iodides.
Scheme 9: The kilogram-scale synthesis of oxetane intermediate 41.
Scheme 10: Overview of the intramolecular opening of 3-membered rings.
Scheme 11: Synthesis of 4,7-dioxatricyclo[3.2.1.03,6]octane skeletons.
Scheme 12: Silicon-directed electrophilic cyclisation of homoallylic alcohols.
Scheme 13: Hydrosilylation–iodocyclisation of homopropargylic alcohols.
Scheme 14: Cu-catalysed intramolecular O-vinylation of γ-bromohomoallylic alcohols.
Scheme 15: Cu-catalysed intramolecular cross-coupling of hydroxyvinylstannanes.
Scheme 16: Isomerisation of oxiranyl ethers containing weakly carbanion-stabilising groups.
Scheme 17: Cyclisation of diethyl haloalkoxymalonates.
Scheme 18: Synthesis of oxetanes through a 1,5-HAT/radical recombination sequence.
Scheme 19: General approach to oxetanes via [2 + 2] cycloadditions.
Scheme 20: Synthesis of tricyclic 4:4:4 oxetanes through a photochemical triple cascade reaction.
Scheme 21: Iridium-catalysed Paternò–Büchi reaction between α-ketoesters and simple alkenes.
Scheme 22: Three-step synthesis of spirocyclic oxetanes 83 via Paternò–Büchi reaction, nucleophilic ring openi...
Scheme 23: Enantioselective Paternò–Büchi reaction catalysed by a chiral iridium photocatalyst.
Scheme 24: Synthesis of polysubstituted oxetanes 92 via Cu(II)-mediated formal [2 + 2] cycloadditions.
Scheme 25: Synthesis of alkylideneoxetanes via NHC- and DBU-mediated formal [2 + 2] cycloadditions.
Scheme 26: Use of sulphur-stabilised carbanions in ring expansions.
Scheme 27: Synthesis of α,α-difluoro(arylthio)methyl oxetanes.
Scheme 28: Ring expansion in an industrial synthesis of PF-06878031.
Scheme 29: Ring contraction of triflated 2-hydroxy-γ-lactones.
Scheme 30: Ring contraction in an industrial synthesis of PF-06878031.
Scheme 31: Photochemical ring contraction of 2,5-dihydrofurans by aryldiazoacetic acid esters.
Scheme 32: Synthesis of 3-oxetanones via O-H insertion of carbenes.
Scheme 33: Synthesis of phosphonate oxetanones via gold-mediated alkyne oxidation/O–H insertion.
Scheme 34: Syntheses and common derivatisations of 3-oxetanone.
Scheme 35: SN1 substitution of 3-aryloxetan-3-ols by thiols and alcohols.
Scheme 36: Fe–Ni dual-catalytic olefin hydroarylation towards 3-alkyl-3-(hetero)aryloxetanes.
Scheme 37: Synthesis of 3-aryloxetan-3-carboxylic acids.
Scheme 38: Decarboxylative alkylation of 3-aryloxetan-3-carboxylic acids.
Scheme 39: Synthesis of 3-amino-3-aryloxetanes via photoredox/nickel cross-coupling catalysis.
Scheme 40: Intermolecular cross-selective [2 + 2] photocycloaddition towards spirooxetanes.
Scheme 41: Synthesis of 3-aryl-3-aminooxetanes via defluorosulphonylative coupling.
Scheme 42: Two-step synthesis of amide bioisosteres via benzotriazolyl Mannich adducts 170.
Scheme 43: Functionalisation of oxetanyl trichloroacetimidates 172.
Scheme 44: Synthesis of oxetane-amino esters 176.
Scheme 45: Tandem Friedel–Crafts alkylation/intramolecular ring opening of 3-aryloxetan-3-ols.
Scheme 46: Synthesis of polysubstituted furans and pyrroles.
Scheme 47: Synthesis of oxazolines and bisoxazolines.
Scheme 48: Tandem, one-pot syntheses of various polycyclic heterocycles.
Scheme 49: Synthesis of 1,2-dihydroquinolines via skeletal reorganisation of oxetanes.
Scheme 50: Synthesis of benzoindolines and 2,3-dihydrobenzofurans and their derivatisations.
Scheme 51: Synthesis of polysubstituted 1,4-dioxanes.
Scheme 52: Preparation of various lactones via ring opening of oxetane-carboxylic acids 219.
Scheme 53: Tsuji-Trost allylation/ring opening of 3-aminooxetanes.
Scheme 54: Arylative skeletal rearrangement of 3-vinyloxetan-3-ols to 2,5-dihydrofurans.
Scheme 55: Reductive opening of oxetanes using catalytic Mg–H species.
Scheme 56: Opening of oxetanes by silyl ketene acetals.
Scheme 57: Rhodium-catalysed hydroacylation of oxetanes.
Scheme 58: Generation of radicals from oxetanes mediated by a vitamin B12-derived cobalt catalyst.
Scheme 59: Reductive opening of oxetanes by B–Si frustrated Lewis pairs.
Scheme 60: Zirconocene-mediated reductive opening of oxetanes.
Scheme 61: Enantioselective syntheses of small and medium-size rings using chiral phosphoric acids.
Scheme 62: Asymmetric synthesis of 2,3-dihydrobenzo[b]oxepines catalysed by a chiral scandium complex.
Scheme 63: Enantioselective synthesis of 1,3-bromohydrins under a chiral squaramide catalysis.
Scheme 64: Enantioselective opening of 2-aryl-2-ethynyloxetanes by anilines.
Scheme 65: Ru-catalysed insertion of diazocarbonyls into oxetanes.
Scheme 66: Ring expansion of oxetanes by stabilised carbenes generated under blue light irradiation.
Scheme 67: Expansion of oxetanes via nickel-catalysed insertion of alkynyltrifluoroborates.
Scheme 68: Nickel-catalysed expansion of oxetanes into ε-caprolactones.
Scheme 69: Expansion of oxetanes via cobalt-catalysed carbonyl insertion.
Scheme 70: Gold-catalysed intramolecular 1,1-carboalkoxylation of oxetane-ynamides.
Scheme 71: Expansion of oxetanes by stabilised sulphoxonium ylides.
Scheme 72: Cu-catalysed ring expansion of 2-vinyloxetanes by diazoesters.
Scheme 73: Total synthesis of (+)-oxetin.
Scheme 74: Total synthesis of racemic oxetanocin A.
Scheme 75: Total synthesis of (−)-merrilactone A.
Scheme 76: Total synthesis of (+)-dictyoxetane.
Scheme 77: Total synthesis of ent-dichrocephone B.
Scheme 78: Total synthesis of (−)-mitrephorone A.
Scheme 79: Total synthesis of (−)-taxol.
Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41
Graphical Abstract
Figure 1: Phosphonopeptides, phosphonodepsipeptides, peptides, and depsipeptides.
Figure 2: The diverse strategies for phosphonodepsipeptide synthesis.
Scheme 1: Synthesis of α-phosphonodepsidipeptides as inhibitors of leucine aminopeptidase.
Figure 3: Structure of 2-hydroxy-2-oxo-3-[(phenoxyacetyl)amino]-1,2-oxaphosphorinane-6-carboxylic acid (16).
Scheme 2: Synthesis of α-phosphonodepsidipeptide 17 as coupling partner for cyclen-containing phosphonodepsip...
Scheme 3: Synthesis of α-phosphonodepsidipeptides containing enantiopure hydroxy ester as VanX inhibitors.
Scheme 4: Synthesis of α-phosphonodepsidipeptides as VanX inhibitors.
Scheme 5: Synthesis of optically active α-phosphonodepsidipeptides as VanX inhibitors.
Scheme 6: The synthesis of phosphonodepsipeptides through a thionyl chloride-catalyzed esterification of N-Cb...
Scheme 7: Synthesis of α-phosphinodipeptidamide as a hapten.
Scheme 8: Synthesis of α-phosphonodepsioctapeptide 41.
Scheme 9: Synthesis of phosphonodepsipeptides via an in situ-generated phosphonochloridate.
Scheme 10: Synthesis of α-phosphonodepsitetrapeptides 58 as inhibitors of the aspartic peptidase pepsin.
Scheme 11: Synthesis of a β-phosphonodepsidipeptide library 64.
Scheme 12: Synthesis of another β-phosphonodepsidipeptide library.
Scheme 13: Synthesis of γ-phosphonodepsidipeptides.
Scheme 14: Synthesis of phosphonodepsipeptides 85 as folylpolyglutamate synthetase inhibitors.
Scheme 15: Synthesis of the γ-phosphonodepsitripeptide 95 as an inhibitor of γ-gutamyl transpeptidase.
Scheme 16: Synthesis of phosphonodepsipeptides as inhibitors and probes of γ-glutamyl transpeptidase.
Scheme 17: Synthesis of phosphonyl depsipeptides 108 via DCC-mediated condensation and oxidation.
Scheme 18: Synthesis of phosphonodepsipeptides 111 with BOP and PyBOP as coupling reagents.
Scheme 19: Synthesis of optically active phosphonodepsipeptides with BOP and PyBOP as coupling reagents.
Scheme 20: Synthesis of phosphonodepsipeptides with BroP and TPyCIU as coupling reagents.
Scheme 21: Synthesis of a phosphonodepsipeptide hapten with BOP as coupling reagent.
Scheme 22: Synthesis of phosphonodepsitripeptide with BOP as coupling reagent.
Scheme 23: Synthesis of norleucine-derived phosphonodepsipeptides 135 and 138.
Scheme 24: Synthesis of norleucine-derived phosphonodepsipeptides 141 and 144.
Scheme 25: Solid-phase synthesis of phosphonodepsipeptides.
Scheme 26: Synthesis of phosphonodepsidipeptides via the Mitsunobu reaction.
Scheme 27: Synthesis of γ-phosphonodepsipeptide via the Mitsunobu reaction.
Scheme 28: Synthesis of phosphonodepsipeptides via a multicomponent condensation reaction.
Scheme 29: Synthesis of phosphonodepsipeptides with a functionalized side-chain via a multicomponent condensat...
Scheme 30: High yielding synthesis of phosphonodepsipeptides via a multicomponent condensation.
Scheme 31: Synthesis of optically active phosphonodepsipeptides via a multicomponent condensation reaction.
Scheme 32: Synthesis of N-phosphoryl phosphonodepsipeptides.
Scheme 33: Synthesis of phosphonodepsipeptides via the alkylation of phosphonic monoesters.
Scheme 34: Synthesis of phosphonodepsipeptides as inhibitors of aspartic protease penicillopepsin.
Scheme 35: Synthesis of phosphonodepsipeptides as prodrugs.
Scheme 36: Synthesis of phosphonodepsithioxopeptides 198.
Scheme 37: Synthesis of phosphonodepsipeptides.
Scheme 38: Synthesis of phosphonodepsipeptides with C-1-hydroxyalkylphosphonic acid.
Scheme 39: Synthesis of phosphonodepsipeptides with C-1-hydroxyalkylphosphonate via the rhodium-catalyzed carb...
Scheme 40: Synthesis of phosphonodepsipeptides with a C-1-hydroxyalkylphosphonate motif via a copper-catalyzed...
Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56
Graphical Abstract
Scheme 1: Synthesis of mixed alkyl alkenyl phosphonates.
Scheme 2: Scope of the copper-catalyzed alkenylation of dialkyl phosphonates. Reactions run on a 0.2 mmol sca...
Beilstein J. Org. Chem. 2015, 11, 1418–1424, doi:10.3762/bjoc.11.153
Graphical Abstract
Figure 1: General structure of bisphosphonates.
Figure 2: General structures of 1-hydroxy- and 1-amino-1-phosphinylalkylphosphonates (2 and 3, respectively) ...
Scheme 1: Electrochemical α-methoxylation of 1-(N-acylamino)alkylphosphonates.
Scheme 2: Transformation of diethyl 1-(N-acetylamino)-1-methoxyalkylphosphonates into bisphosphoric acid este...
Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6
Graphical Abstract
Scheme 1: Monodentate phosphorus ligands, e.g. BINOL-based phosphoramidites or TADDOL-based phosphites, are h...
Scheme 2: Modular phosphoramidites (R= NR'2) or phosphites (R= OR') from reactive chlorophosphite intermediat...
Figure 1: X-ray crystal structure of BIFOP-Cl (1). Distances are given in Å. (BAA = biaryl angle between C2-C1...
Figure 2: X-ray structures of BIFOP-Br (2). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C2...
Scheme 3: Synthesis of biphenyl-2,2'-bisfenchol (BIFOL) based phosphane derivatives (BIFOPs).
Figure 3: X-ray structures of BIFOP-H (3). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C2...
Figure 4: X-ray structures of BIFOP-nBu (5). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'-C...
Figure 5: X-ray structures of BIFOP(O)-H (8). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1'...
Figure 6: X-ray structures of phosphite BIFOP-OPh (6). Distances are given in Å. (BAA = biaryl angle between C...
Figure 7: X-ray structures of phosphoramidite BIFOP-NEt2 (7). Distances are given in Å. (BAA = biaryl angle b...
Figure 8: X-ray structures of BIFOP(O)-Cl (9). Distances are given in Å. (BAA = biaryl angle between C2-C1-C1...
Scheme 4: Geometries of BIFOP-systems with respect to biaryl dihedral angles (C2-C1-C1’-C2’, BAA), fenchyl-ar...
Figure 9: Computed geometry (PM3) of plus-(P)-BIFOP-Cl with unnatural plus-(P)-biaryl conformation. Distances...
Scheme 5: Biphenyl-2,2'-bisfenchol based phosphanes (BIFOPs) as chiral ligands in enantioselective Cu-catalyz...
Scheme 6: Anharmonic B3LYP/6-31G*(C,H,N,O,F,Cl,Br) /SDD(Cu) CO-stretching frequencies to assess metal to liga...
Beilstein J. Org. Chem. 2005, 1, No. 3, doi:10.1186/1860-5397-1-3
Graphical Abstract
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