2-Phospha[3]ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations.

PubWeight™: 1.31‹?› | Rank: Top 10%

🔗 View Article (PMID 18834118)

Published in J Am Chem Soc on October 04, 2008

Authors

Arnaud Voituriez1, Armen Panossian, Nicolas Fleury-Brégeot, Pascal Retailleau, Angela Marinetti

Author Affiliations

1: Institut de Chimie des Substances Naturelles, CNRS UPR 2301-1, av. de la Terrasse, 91198 Gif-sur-Yvette, France.

Articles citing this

Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles. Angew Chem Int Ed Engl (2009) 1.67

Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines. J Am Chem Soc (2009) 1.16

Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs. Chem Commun (Camb) (2013) 1.14

Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters. J Am Chem Soc (2011) 1.14

Phosphine catalysis of allenes with electrophiles. Chem Soc Rev (2014) 1.02

Chiral phosphines in nucleophilic organocatalysis. Beilstein J Org Chem (2014) 1.01

Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways. J Am Chem Soc (2011) 0.99

PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE. Organic Synth (2009) 0.91

Biphenyl-derived phosphepines as chiral nucleophilic catalysts: enantioselective [4+1] annulations to form functionalized cyclopentenes. Angew Chem Int Ed Engl (2014) 0.86

Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction. Chemistry (2011) 0.86

Hydroxyproline-derived pseudoenantiomeric [2.2.1] bicyclic phosphines: asymmetric synthesis of (+)- and (-)-pyrrolines. J Am Chem Soc (2014) 0.84

Phosphine-catalyzed enantioselective intramolecular [3+2] annulations to generate fused ring systems. J Am Chem Soc (2015) 0.81

Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence. Nat Commun (2014) 0.77

Enantioselective [3 + 2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine. Beilstein J Org Chem (2016) 0.77

Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates with maleimides. Beilstein J Org Chem (2012) 0.77

PHOSPHINE-CATALYZED [3 + 2] ANNULATION: SYNTHESIS OF ETHYL 5-(tert-BUTYL)-2-PHENYL-1-TOSYL-3-PYRROLINE-3-CARBOXYLATE. Organic Synth (2012) 0.76

Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations. Aldrichimica Acta (2016) 0.75

Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates. Adv Synth Catal (2012) 0.75

Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones via regiodivergent [3 + 2] annulations of aurones and an allenoate. Chem Sci (2017) 0.75

Phosphine-catalyzed enantioselective [3 + 2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones. Chem Sci (2017) 0.75

Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid. Chem Sci (2017) 0.75

From Mechanistic Study to Chiral Catalyst Optimization: Theoretical Insight into Binaphthophosphepine-catalyzed Asymmetric Intramolecular [3 + 2] Cycloaddition. Sci Rep (2017) 0.75

Articles by these authors

Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction. J Am Chem Soc (2009) 1.21

Protein crystallography under xenon and nitrous oxide pressure: comparison with in vivo pharmacology studies and implications for the mechanism of inhaled anesthetic action. Biophys J (2006) 1.19

Boron asymmetry in a BODIPY derivative. Org Lett (2010) 1.17

Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion. J Am Chem Soc (2012) 1.04

Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates. Org Lett (2011) 1.00

Synthesis of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process. Org Lett (2006) 0.99

A strategy for the stereoselective synthesis of unsymmetric atropisomeric ligands: preparation of NAPhePHOS, a new biaryl diphosphine. Chemistry (2002) 0.96

Synthesis and minisci reactions of organotrifluoroborato building blocks. J Org Chem (2013) 0.93

Synthesis of protected chiral vicinal diaminoalcohols by diastereoselective intramolecular benzylic substitution from bistrichloroacetimidates. Org Lett (2007) 0.92

A rational protocol for the synthesis of arylated bipyridine ligands via a cycloaddition pathway. J Org Chem (2007) 0.92

Highly enantioselective electrophilic α-bromination of enecarbamates: chiral phosphoric acid and calcium phosphate salt catalysts. J Am Chem Soc (2012) 0.92

Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling. J Org Chem (2003) 0.91

Kingianin A: a new natural pentacyclic compound from Endiandra kingiana. Org Lett (2010) 0.90

Intermolecular C-H amination of complex molecules: insights into the factors governing the selectivity. J Org Chem (2012) 0.90

{2-[(2-Acetyl-hydrazin-1-yl-idene)methyl-κN,O]-6-methoxy-phenolato-κO}(nitrato-κO)copper(II) monohydrate. Acta Crystallogr Sect E Struct Rep Online (2010) 0.90

Catalytic oxyamidation of indoles. Angew Chem Int Ed Engl (2010) 0.90

Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides. Tetrahedron Lett (2012) 0.90

An organocatalytic [3+2] cyclisation strategy for the highly enantioselective synthesis of spirooxindoles. Chemistry (2010) 0.89

Transition-metal-free atropo-selective synthesis of biaryl compounds based on arynes. Chemistry (2012) 0.88

Trifluoromethyl ethers and -thioethers as tools for medicinal chemistry and drug discovery. Curr Top Med Chem (2014) 0.88

Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations. Chem Commun (Camb) (2010) 0.86

Antiplasmodial benzophenones from the trunk latex of Moronobea coccinea (Clusiaceae). Phytochemistry (2008) 0.85

Chiral phosphoric acid catalyzed inverse-electron-demand aza-Diels-Alder reaction of isoeugenol derivatives. Org Lett (2012) 0.84

Expanding the scope of enantioselective ferroPHANE-promoted [3+2] annulations with alpha,beta-unsaturated ketones. Chemistry (2010) 0.84

Stereochemistry, total synthesis, and biological evaluation of the new plant hormone solanacol. Chemistry (2010) 0.84

Phosphine-phosphinite and phosphine-phosphite ligands: preparation and applications in asymmetric catalysis. Chem Rev (2011) 0.84

Palladium-catalyzed domino intramolecular N-arylation/intermolecular C-C bond formation for the synthesis of functionalized benzodiazepinediones. Org Lett (2008) 0.83

2-(2'-Hydroxyphenyl)benzimidazole and 9,10-phenanthroimidazole chelates and borate complexes: solution- and solid-state emitters. Org Lett (2013) 0.83

Platinum(II) catalysts for highly enantioselective 1,6-enyne cycloisomerizations. synthetic, structural, and catalytic studies. Org Lett (2009) 0.82

New access to trisubstituted 3-pyrrolines under phosphine catalysis. Org Lett (2009) 0.82

Palladium-catalyzed domino process to spirooxindoles: ligand effect on aminopalladation versus carbopalladation. Chemistry (2010) 0.82

6,6-Spiroimine analogs of (-)-gymnodimine A: synthesis and biological evaluation on nicotinic acetylcholine receptors. Org Biomol Chem (2011) 0.82

Cinchona alkaloid amide catalyzed enantioselective formal [2+2] cycloadditions of allenoates and imines: synthesis of 2,4-disubstituted azetidines. Angew Chem Int Ed Engl (2011) 0.81

Structure of sylvaticin, a new alpha-elicitin-like protein from Pythium sylvaticum. Acta Crystallogr D Biol Crystallogr (2007) 0.81

Isocyanate-, isothiocyanate-, urea-, and thiourea-substituted boron dipyrromethene dyes as fluorescent probes. J Org Chem (2006) 0.81

N-heterocyclic carbene-amine Pt(II) complexes, a new chemical space for the development of platinum-based anticancer drugs. J Med Chem (2010) 0.81

Axiphenylalaninium and axityrosinium, modified amino acids from the Mediterranean marine sponge Axinella polypoides. J Nat Prod (2009) 0.81

1H-phosphindoles as structural units in the synthesis of chiral helicenes. Angew Chem Int Ed Engl (2012) 0.81

Palladium-catalyzed intramolecular C(sp(3))--H functionalization: catalyst development and synthetic applications. Chemistry (2007) 0.81

Solid-state gas sensors developed from functional difluoroboradiazaindacene dyes. Chemistry (2009) 0.81

Highly enantioselective aza-Diels-Alder reaction of 1-azadienes with enecarbamates catalyzed by chiral phosphoric acids. Angew Chem Int Ed Engl (2013) 0.80

White emitters by tuning the excited-state intramolecular proton-transfer fluorescence emission in 2-(2'-hydroxybenzofuran)benzoxazole dyes. Chemistry (2014) 0.79

Rhodium-catalyzed intramolecular formation of N-sulfamoyl 2,3-aziridino-γ-lactones and their use for the enantiospecific synthesis of α,β-diamino acid derivatives. J Org Chem (2012) 0.79

Helicenes with embedded phosphole units in enantioselective gold catalysis. Angew Chem Int Ed Engl (2013) 0.79

Bioactive polyketides isolated from agar-supported fermentation of Phomopsis sp. CMU-LMA, taking advantage of the scale-up device, Platotex. Phytochemistry (2013) 0.79

Jatrophane diterpenes as inhibitors of chikungunya virus replication: structure-activity relationship and discovery of a potent lead. J Nat Prod (2014) 0.78

Phosphine-catalyzed synthesis of 3,3-spirocyclopenteneoxindoles from γ-substituted allenoates: systematic studies and targeted applications. J Org Chem (2013) 0.78

Antitumor trans-N-heterocyclic carbene-amine-Pt(II) complexes: synthesis of dinuclear species and exploratory investigations of DNA binding and cytotoxicity mechanisms. J Med Chem (2013) 0.78

Aziridines from intramolecular alkene aziridination of sulfamates: reactivity toward carbon nucleophiles. application to the synthesis of spisulosine and its fluoro analogue. J Org Chem (2011) 0.78

Highly diastereoselective three-component vinylogous Mannich reaction between isoquinolines, acyl/sulfonyl chlorides, and silyloxyfurans. Org Lett (2009) 0.78

Chemistry at boron: synthesis and properties of red to near-IR fluorescent dyes based on boron-substituted diisoindolomethene frameworks. J Org Chem (2011) 0.78

Phosphahelicenes in asymmetric organocatalysis: [3+2] cyclizations of γ-substituted allenes and electron-poor olefins. Angew Chem Int Ed Engl (2015) 0.78

Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives. J Nat Prod (2012) 0.78

Phosphorus-containing [2]catenanes as an example of interlocking chiral structures. Angew Chem Int Ed Engl (2006) 0.78

Excited-state absorption properties of platinum(II) terpyridyl acetylides. Inorg Chem (2007) 0.77

Synthesis of 3,3'-spirocyclic oxindoles via phosphine catalyzed [4 + 2] cyclizations. Org Lett (2013) 0.77

Catalytic intermolecular alkene oxyamination with nitrenes. Chemistry (2014) 0.77

Oxidative coupling of 1,7,8-unsubstituted BODIPYs: synthesis and electrochemical and spectroscopic properties. J Org Chem (2012) 0.77

Cytotoxic pentacyclic triterpenoids from Combretum sundaicum and Lantana camara as inhibitors of Bcl-xL/BakBH3 domain peptide interaction. J Nat Prod (2009) 0.77

Ethynyl-boron subphthalocyanines displaying efficient cascade energy transfer and large Stokes shifts. Angew Chem Int Ed Engl (2008) 0.77

Transition-metal-free tunable chemoselective N functionalization of indoles with ynamides. Angew Chem Int Ed Engl (2014) 0.77

Synthesis of water-soluble red-emitting thienyl-BODIPYs and bovine serum albumin labeling. Chemistry (2014) 0.77

Unsymmetrical p-carborane backbone as a linker for donor-acceptor dyads. Chemistry (2012) 0.77

Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes. Org Lett (2011) 0.77

Terpyridine-functionalized imidazolium ionic liquids. Chem Commun (Camb) (2009) 0.77

Efficient synthesis of panchromatic dyes for energy concentration. Angew Chem Int Ed Engl (2010) 0.77

Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine. J Org Chem (2009) 0.77

High-performance solution-processed solar cells and ambipolar behavior in organic field-effect transistors with thienyl-BODIPY scaffoldings. J Am Chem Soc (2012) 0.77

Substituted diketopyrrolopyrroles as input energy units in soluble donor-acceptor dyads. Chemistry (2010) 0.77

Catalytic selective oxyamidation of cyclic enamides using nitrenes. Chemistry (2011) 0.77

Studies on the formal [3 + 2] cycloaddition of aziridines with alkenes for the synthesis of 1-azaspiroalkanes. J Org Chem (2015) 0.77

Copper(I) catalyzed regioselective asymmetric alkoxyamination of aryl enamide derivatives. Org Lett (2011) 0.76

Biomimetically inspired short access to the 2-aminoimidazole-fused tetracyclic core of (+/-)-dibromoagelaspongin. Org Lett (2009) 0.76

Borondipyrromethene dyes with pentane-2,4-dione anchors. Org Lett (2010) 0.76

Chiral phosphoric acid-catalyzed enantioselective three-component Povarov reaction using cyclic enethioureas as dienophiles: stereocontrolled access to enantioenriched hexahydropyrroloquinolines. Chemistry (2012) 0.76

Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity. Planta Med (2008) 0.76

Diastereoselective synthesis of dibenzoazepines through chelation on palladium(IV) intermediates. Org Lett (2013) 0.76

Synthesis, biological evaluation, and molecular modeling of natural and unnatural flavonoidal alkaloids, inhibitors of kinases. J Med Chem (2012) 0.76

Phosphathiahelicenes: synthesis and uses in enantioselective gold catalysis. Chemistry (2014) 0.76

Boron dipyrromethene (Bodipy) phosphorescence revealed in [Ir(ppy)(2)(bpy-C[triple bond]C-bodipy)](+). Inorg Chem (2010) 0.76

Highly substituted Bodipy dyes with spectroscopic features sensitive to the environment. J Org Chem (2011) 0.76

Catalytic enantioselective vinylogous Mukaiyama-Michael addition of 2-silyloxyfurans to cyclic unsaturated oxo esters. J Org Chem (2013) 0.75

α-Fused dithienyl BODIPYs synthesized by oxidative ring closure. Org Lett (2014) 0.75

Dichlorido{N'-[phen-yl(pyridin-2-yl-κN)methyl-idene]isonicotinohydrazide-κ(2)N',O}zinc. Acta Crystallogr Sect E Struct Rep Online (2013) 0.75

Hydro-nium (3-oxo-1-phosphono-1,3-dihydro-isobenzofuran-1-yl)phospho-nate. Acta Crystallogr Sect E Struct Rep Online (2009) 0.75

Bis(N,N'-dimethyl-ethylenediammonium) tris-(oxalato-κO,O)cobaltate(II) dihydrate: an ion-pair complex. Acta Crystallogr Sect E Struct Rep Online (2011) 0.75

Methyl [hydr-oxy(phen-yl)phosphono-meth-yl]phospho-nate methanol solvate. Acta Crystallogr Sect E Struct Rep Online (2008) 0.75