Palladium-catalyzed [3 + 3] cycloaddition of trimethylenemethane with azomethine imines.

PubWeight™: 1.10‹?› | Rank: Top 10%

🔗 View Article (PMID 16683793)

Published in J Am Chem Soc on May 17, 2006

Authors

Ryo Shintani1, Tamio Hayashi

Author Affiliations

1: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

Articles citing this

Highly stereoselective formal [3 + 3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes. J Am Chem Soc (2007) 1.82

Discovering New Reactions with N-Heterocyclic Carbene Catalysis. Aldrichimica Acta (2009) 1.32

Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates. J Am Chem Soc (2011) 1.24

Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters. J Am Chem Soc (2009) 1.03

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

Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis. Curr Org Synth (2010) 0.98

Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines. Tetrahedron (2008) 0.91

Synthesis of tetrahydropyridazines by a metal-carbene-directed enantioselective vinylogous N-H insertion/Lewis acid-catalyzed diastereoselective Mannich addition. Angew Chem Int Ed Engl (2012) 0.90

Total synthesis of (+)-lepadin F. Org Lett (2008) 0.90

Bicyclic pyrazolidinone derivatives from diastereoselective catalytic [3 + 3]-cycloaddition reactions of enoldiazoacetates with azomethine imines. Org Lett (2013) 0.87

Highly selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-methylene-β-silyloxy-β-amido-α-diazoacetates. J Am Chem Soc (2013) 0.83

Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone. Chem Commun (Camb) (2013) 0.82

Highly enantioselective dearomatizing formal [3+3] cycloaddition reactions of N-acyliminopyridinium ylides with electrophilic enol carbene intermediates. Angew Chem Int Ed Engl (2013) 0.81

A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II. Synlett (2008) 0.81

A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation. Synthesis (Stuttg) (2009) 0.77

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

Articles by these authors

Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds. Org Lett (2004) 1.10

Iron-catalyzed Grignard cross-coupling with alkyl halides possessing beta-hydrogens. Org Lett (2004) 1.10

Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. Org Lett (2009) 1.03

Rhodium-catalyzed asymmetric construction of quaternary carbon stereocenters: ligand-dependent regiocontrol in the 1,4-addition to substituted maleimides. J Am Chem Soc (2006) 1.03

Rhodium-catalyzed isomerization of alpha-arylpropargyl alcohols to indanones: involvement of an unexpected reaction cascade. J Am Chem Soc (2005) 0.97

Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides. Chem Commun (Camb) (2009) 0.96

Metathesis route to bridged metallocenes. J Am Chem Soc (2002) 0.95

tert-Butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative. J Am Chem Soc (2010) 0.94

Copper-catalyzed asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates. Angew Chem Int Ed Engl (2011) 0.94

Sodium tetraarylborates as effective nucleophiles in rhodium/diene-catalyzed 1,4-addition to beta,beta-disubstituted alpha,beta-unsaturated ketones: catalytic asymmetric construction of quaternary carbon stereocenters. J Am Chem Soc (2009) 0.93

Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines. Chem Commun (Camb) (2009) 0.92

Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as mild and reproducible agents for rhodium-catalyzed 1,4-addition reactions. J Am Chem Soc (2007) 0.92

Rhodium-catalyzed isomerization of unactivated alkynes to 1,3-dienes. Chem Commun (Camb) (2006) 0.91

Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins. Angew Chem Int Ed Engl (2006) 0.91

Iridium/chiral diene-catalyzed asymmetric 1,6-addition of arylboroxines to alpha,beta,gamma,delta-unsaturated carbonyl compounds. J Am Chem Soc (2010) 0.90

Cross-Coupling of Aryl Halides and Allyl Acetates with Arylboron Reagents in Water Using an Amphiphilic Resin-Supported Palladium Catalyst. J Org Chem (1999) 0.90

C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines. J Am Chem Soc (2004) 0.90

Arylmagnesiation of alkynes catalyzed cooperatively by iron and copper complexes. J Am Chem Soc (2005) 0.90

Preparation of an amphiphilic resin-supported BINAP ligand and its use for rhodium-catalyzed asymmetric 1,4-addition of phenylboronic acid in water. Org Lett (2004) 0.89

A kinetic study on Rh/binap-catalyzed 1,4-addition of phenylboronic acid to enones: negative nonlinear effect caused by predominant homochiral dimer contribution. J Am Chem Soc (2006) 0.89

Catalytic asymmetric synthesis of allylsilanes through rhodium/chiral diene-catalyzed 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes. Org Lett (2007) 0.88

Asymmetric synthesis of metallocenes through enantioselective addition of organolithium reagents to 6-(dimethylamino)fulvene. J Org Chem (2002) 0.87

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine. Org Lett (2005) 0.87

Design and Preparation of 3,3'-Disubstituted 2,2'-Bis(oxazolyl)-1,1'-binaphthyls (boxax): New Chiral Bis(oxazoline) Ligands for Catalytic Asymmetric Wacker-Type Cyclization. J Org Chem (1999) 0.87

Palladium-catalyzed asymmetric [3+3] cycloaddition of trimethylenemethane derivatives with nitrones. Angew Chem Int Ed Engl (2007) 0.86

Preparation of C2-symmetric bicyclo[2.2.2]octa-2,5-diene ligands and their use for rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids. J Org Chem (2005) 0.86

Expanding the C2-symmetric bicyclo[2.2.1]hepta-2,5-diene ligand family: concise synthesis and catalytic activity in rhodium-catalyzed asymmetric addition. J Org Chem (2006) 0.85

Asymmetric synthesis of 1-aryl-1,2-ethanediols from arylacetylenes by palladium-catalyzed asymmetric hydrosilylation as a key step. J Am Chem Soc (2002) 0.85

Chiral tetrafluorobenzobarrelenes as effective ligands for rhodium-catalyzed asymmetric 1,4-addition of arylboroxines to beta,beta-disubstituted alpha,beta-unsaturated ketones. Angew Chem Int Ed Engl (2010) 0.85

Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane. Org Lett (2005) 0.85

Iron-copper cooperative catalysis in the reactions of alkyl Grignard reagents: exchange reaction with alkenes and carbometalation of alkynes. J Am Chem Soc (2011) 0.84

Chiral phosphine-olefin ligands in the rhodium-catalyzed asymmetric 1,4-addition reactions. J Am Chem Soc (2007) 0.84

Asymmetric synthesis of (triaryl)methylamines by rhodium-catalyzed addition of arylboroxines to cyclic N-sulfonyl ketimines. J Am Chem Soc (2012) 0.84

Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation. Angew Chem Int Ed Engl (2009) 0.84

Rhodium-catalyzed asymmetric [5+2] cycloaddition of alkyne-vinylcyclopropanes. Chemistry (2009) 0.84

Catalytic asymmetric arylative cyclization of alkynals: phosphine-free rhodium/diene complexes as efficient catalysts. J Am Chem Soc (2005) 0.83

Hydroxorhodium/chiral diene complexes as effective catalysts for the asymmetric arylation of 3-aryl-3-hydroxyisoindolin-1-ones. Angew Chem Int Ed Engl (2013) 0.83

Rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids. J Am Chem Soc (2006) 0.83

Kinetic studies prove high catalytic activity of a diene-rhodium complex in 1,4-addition of phenylboronic acid to alpha,beta-unsaturated ketones. Chem Asian J (2006) 0.83

A new entry of nucleophiles in rhodium-catalyzed asymmetric 1,4-addition reactions: addition of organozinc reagents for the synthesis of 2-aryl-4-piperidones. J Am Chem Soc (2004) 0.83

Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes. Org Lett (2009) 0.83

Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated Weinreb amides. Chem Commun (Camb) (2005) 0.83

Cobalt-catalyzed asymmetric 1,6-addition of (triisopropylsilyl)-acetylene to α,β,γ,δ-unsaturated carbonyl compounds. J Am Chem Soc (2012) 0.82

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines. Org Lett (2005) 0.82

Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones. J Am Chem Soc (2008) 0.82

Palladium-catalyzed silylation of alcohols with hexamethyldisilane. Chem Commun (Camb) (2006) 0.82

Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions. Org Lett (2008) 0.82

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates. Org Lett (2008) 0.82

Palladium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzosiloles via enantioselective C-H bond functionalization. J Am Chem Soc (2012) 0.82

Iron-catalyzed oxidative homo-coupling of aryl Grignard reagents. Org Lett (2005) 0.82

Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction. Org Lett (2005) 0.82

Rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones. J Am Chem Soc (2007) 0.81

Gamma-methylidene-delta-valerolactones as a coupling partner for cycloaddition: palladium-catalyzed [4 + 3] cycloaddition with nitrones. J Am Chem Soc (2007) 0.81

Chiral tetrafluorobenzobarrelene ligands for the rhodium-catalyzed asymmetric cycloisomerization of oxygen- and nitrogen-bridged 1,6-enynes. Angew Chem Int Ed Engl (2010) 0.81

A new type of catalytic tandem 1,4-addition-aldol reaction which proceeds through an (oxa-pi-allyl)rhodium intermediate. J Am Chem Soc (2002) 0.81

Chiral phosphine-olefin bidentate ligands in asymmetric catalysis: rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to maleimides. Angew Chem Int Ed Engl (2005) 0.81

A new cine-substitution of alkenyl sulfones with aryltitanium reagents catalyzed by rhodium: mechanistic studies and catalytic asymmetric synthesis of allylarenes. J Am Chem Soc (2003) 0.81

Iron-catalyzed oxidative coupling of alkylamides with arenes through oxidation of alkylamides followed by Friedel-Crafts alkylation. J Org Chem (2010) 0.81

Highly chemo- and enantioselective arylative cyclization of alkyne-tethered electron-deficient olefins catalyzed by rhodium complexes with chiral dienes. Angew Chem Int Ed Engl (2005) 0.80

Rhodium-catalyzed asymmetric conjugate addition of arylboroxines to borylalkenes: asymmetric synthesis of β-arylalkylboranes. Angew Chem Int Ed Engl (2010) 0.80

Nickel-catalyzed asymmetric grignard cross-coupling of dinaphthothiophene giving axially chiral 1,1'-binaphthyls. J Am Chem Soc (2002) 0.80

Chiral diene-phosphine tridentate ligands for rhodium-catalyzed asymmetric cycloisomerization of 1,6-enynes. Org Lett (2011) 0.80

Palladium-catalyzed asymmetric synthesis of axially chiral (allenylmethyl)silanes and chirality transfer to stereogenic carbon centers in S(E)' reactions. Org Lett (2003) 0.80

Rhodium-catalyzed rearrangement of aryl bis(alkynyl) carbinols to 3-alkynyl-1-indanones. Angew Chem Int Ed Engl (2008) 0.80

Rhodium-catalyzed multicomponent-coupling reactions involving a carborhodation-cross-coupling sequence. Org Lett (2006) 0.80

Cobalt-catalyzed asymmetric addition of silylacetylenes to oxa- and azabenzonorbornadienes. Chem Commun (Camb) (2012) 0.80

Rhodium-catalyzed asymmetric addition of arylboronic acids to beta-phthaliminoacrylate esters toward the synthesis of beta-amino acids. J Am Chem Soc (2010) 0.80

Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines giving 3-arylpyrrolidines: protonation as a key step. J Am Chem Soc (2013) 0.79

Mizoroki-heck-type reaction mediated by potassium tert-butoxide. Angew Chem Int Ed Engl (2011) 0.79

Palladium-catalyzed intramolecular decarboxylative allylic arylation of alpha-aryl-gamma-methylidene-delta-valerolactones. Chem Commun (Camb) (2010) 0.79

Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines. Org Lett (2006) 0.79

Iron-catalyzed arylmagnesiation of aryl(alkyl)acetylenes in the presence of an N-heterocyclic carbene ligand. Org Lett (2007) 0.79

Rhodium-catalyzed asymmetric 1,4-addition of sodium tetraarylborates to β,β-disubstituted α,β-unsaturated esters. Org Lett (2010) 0.79

Rhodium-catalyzed aryl transfer from trisubstituted aryl methanols to alpha,beta-unsaturated carbonyl compounds. Angew Chem Int Ed Engl (2007) 0.79

Copper-catalyzed 1,4-addition of organoboronates to alkylidene cyanoacetates: mechanistic insight and application to asymmetric catalysis. Angew Chem Int Ed Engl (2011) 0.79

High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-addition of arylboroxines to alpha,beta-unsaturated ketones. Org Lett (2006) 0.79

Rhodium-catalyzed asymmetric conjugate alkynylation of enones with alkynylsilanols. Org Lett (2009) 0.79

Synthesis of enantiomerically pure P-stereogenic diphosphacrowns and their palladium complexes. J Org Chem (2011) 0.79

Platinum-catalyzed addition of dimethylsilylene to beta-methyl alpha,beta-unsaturated ketones: gamma-silylation forming 1-oxa-2-silacyclohex-5-enes. Org Lett (2007) 0.79

A cationic rhodium-chiral diene complex as a high-performance catalyst for the intramolecular asymmetric [4+2] cycloaddition of alkyne-1,3-dienes. Angew Chem Int Ed Engl (2007) 0.79

Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with imines. Org Lett (2009) 0.78

Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides. J Am Chem Soc (2012) 0.78

Rhodium-catalyzed asymmetric ring-opening alkynylation of azabenzonorbornadienes. Org Lett (2008) 0.78

Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to alpha,beta-unsaturated ketones. Proc Natl Acad Sci U S A (2004) 0.78

Asymmetric synthesis of axially chiral biaryls by nickel-catalyzed grignard cross-coupling of dibenzothiophenes. J Org Chem (2004) 0.78

Electronic tuning of chiral diene ligands in iridium-catalyzed asymmetric 1,6-addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones. Chem Commun (Camb) (2011) 0.78

Rhodium-catalyzed aryl- and alkylation-oligomerization of alkynoates with organoboron reagents giving salicylates. Chem Commun (Camb) (2010) 0.78

Tuning the chiral environment of C2-symmetric diene ligands: development of 3,7-disubstituted bicyclo[3.3.1]nona-2,6-dienes. J Org Chem (2009) 0.78

Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5-cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride. Org Lett (2005) 0.78