Mechanistic investigation of the palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isocyanates: kinetic studies and origin of the site selectivity in the nucleophilic attack at a (pi-allyl)palladium.

PubWeight™: 0.76‹?›

🔗 View Article (PMID 20450179)

Published in J Am Chem Soc on June 02, 2010

Authors

Ryo Shintani1, Takaoki Tsuji, Soyoung Park, Tamio Hayashi

Author Affiliations

1: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. shintani@kuchem.kyoto-u.ac.jp

Articles by these authors

The von Economo neurons in frontoinsular and anterior cingulate cortex in great apes and humans. Brain Struct Funct (2010) 1.71

Palladium-catalyzed [3 + 3] cycloaddition of trimethylenemethane with azomethine imines. J Am Chem Soc (2006) 1.10

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

Impacts of changes in climate and land use/land cover under IPCC RCP scenarios on streamflow in the Hoeya River Basin, Korea. Sci Total Environ (2013) 1.08

The von Economo neurons in the frontoinsular and anterior cingulate cortex. Ann N Y Acad Sci (2011) 1.07

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

Assessment of exposure to heavy metals and health risks among residents near abandoned metal mines in Goseong, Korea. Environ Pollut (2013) 0.99

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

The von Economo neurons in apes and humans. Am J Hum Biol (2010) 0.96

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

Zolpidem use and risk of fracture in elderly insomnia patients. J Prev Med Public Health (2012) 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

Reciprocal regulation of the autophosphorylation of enzyme INtr by glutamine and α-ketoglutarate in Escherichia coli. Mol Microbiol (2013) 0.93

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

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

Ruthenium-catalyzed Heck-type olefination and Suzuki coupling reactions: studies on the nature of catalytic species. J Am Chem Soc (2004) 0.91

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

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

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

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

Detection of BRAF(V600E) Mutations in Papillary Thyroid Carcinomas by Peptide Nucleic Acid Clamp Real-Time PCR: A Comparison with Direct Sequencing. Korean J Pathol (2012) 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

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

BRAF (V600E) mutation analysis in papillary thyroid carcinomas by peptide nucleic acid clamp real-time PCR. Ann Surg Oncol (2012) 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

Carvacrol prevents diet-induced obesity by modulating gene expressions involved in adipogenesis and inflammation in mice fed with high-fat diet. J Nutr Biochem (2011) 0.88

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

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

Moritella dasanensis sp. nov., a psychrophilic bacterium isolated from the Arctic ocean. Int J Syst Evol Microbiol (2008) 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

The effects of detraining on blood adipokines and antioxidant enzyme in Korean overweight children. Eur J Pediatr (2011) 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

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

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

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

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

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

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

Structure-activity relationships of simplified resiniferatoxin analogues with potent VR1 agonism elucidates an active conformation of RTX for VR1 binding. Bioorg Med Chem (2004) 0.83

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

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 recessive mutation resulting in a disabling amino acid substitution (T194R) in the LHX3 homeodomain causes combined pituitary hormone deficiency. Horm Res Paediatr (2012) 0.83

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

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

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

Direct quantification of loop interaction and π-π stacking for G-quadruplex stability at the submolecular level. J Am Chem Soc (2014) 0.82

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

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

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

The BRAF mutation is associated with the prognosis in colorectal cancer. J Cancer Res Clin Oncol (2014) 0.82

Functional neuroanatomy of emotion processing in major depressive disorder is altered after successful antidepressant therapy. J Psychopharmacol (2012) 0.82

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

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

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

Indole-3-carbinol prevents diet-induced obesity through modulation of multiple genes related to adipogenesis, thermogenesis or inflammation in the visceral adipose tissue of mice. J Nutr Biochem (2012) 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

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

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

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

Developmental analysis and influence of genetic background on the Lhx3 W227ter mouse model of combined pituitary hormone deficiency disease. Endocrinology (2013) 0.80

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

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

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