Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; application to the synthesis of CDP-840.

PubWeight™: 0.83‹?›

🔗 View Article (PMID 12876742)

Published in Angew Chem Int Ed Engl on July 21, 2003

Authors

Varinder K Aggarwal1, Imhyuck Bae, Hee-Yoon Lee, Jeffery Richardson, David T Williams

Author Affiliations

1: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK. v.aggarwal@bristol.ac.uk

Articles by these authors

Global distribution of novel rhinovirus genotype. Emerg Infect Dis (2008) 2.03

Reassortant highly pathogenic influenza A(H5N6) virus in Laos. Emerg Infect Dis (2015) 1.54

Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. J Am Chem Soc (2005) 1.22

The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions. Chem Commun (Camb) (2003) 1.20

Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity. Angew Chem Int Ed Engl (2007) 1.14

Novel oxidative modifications in redox-active cysteine residues. Mol Cell Proteomics (2010) 1.12

Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: dichotomy via a common pathway. J Org Chem (2008) 0.98

Catalytic asymmetric Nazarov reactions promoted by chiral Lewis acid complexes. Org Lett (2003) 0.97

Unraveling the mechanism of epoxide formation from sulfur ylides and aldehydes. J Am Chem Soc (2002) 0.96

Genetic characterization of K13965, a strain of Oak Vale virus from Western Australia. Virus Res (2011) 0.93

A facile access to N-sulfonylimidates and their synthetic utility for the transformation to amidines and amides. Org Lett (2006) 0.93

A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities. J Am Chem Soc (2003) 0.93

Soluble epoxide hydrolase activity determines the severity of ischemia-reperfusion injury in kidney. PLoS One (2012) 0.92

Reactivity and selectivity in the Wittig reaction: a computational study. J Am Chem Soc (2006) 0.92

CP-690550, a Janus kinase inhibitor, suppresses CD4+ T-cell-mediated acute graft-versus-host disease by inhibiting the interferon-γ pathway. Transplantation (2010) 0.91

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimethylsilyl)diazomethane in a regiospecific and highly stereoselective manner. J Am Chem Soc (2002) 0.90

Total synthesis of citrafungin A. J Org Chem (2008) 0.90

Asymmetric sulfonium ylide mediated cyclopropanation: stereocontrolled synthesis of (+)-LY354740. Chemistry (2005) 0.86

Structural and functional insights into the interaction of echoviruses and decay-accelerating factor. J Biol Chem (2005) 0.84

Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates. J Am Chem Soc (2006) 0.84

Total synthesis of aigialomycin D using a one-pot ketene generation-trapping-aromatization sequence. Org Lett (2009) 0.84

Genetic divergence among members of the Kokobera group of flaviviruses supports their separation into distinct species. J Gen Virol (2013) 0.83

Chromen-based TNF-alpha converting enzyme (TACE) inhibitors: design, synthesis, and biological evaluation. Bioorg Med Chem (2007) 0.83

Phorbaketals A, B, and C, sesterterpenoids with a spiroketal of hydrobenzopyran moiety isolated from the marine sponge Phorbas sp. Org Lett (2009) 0.82

Tandem cycloaddition reactions of allenyl diazo compounds forming triquinanes via trimethylenemethane diyls. J Am Chem Soc (2011) 0.81

Initial catalyst-substrate association step in enyne metathesis catalyzed by grubbs ruthenium complex probed by time-dependent fluorescence quenching. J Am Chem Soc (2008) 0.80

Correlation between functionality preference of Ru carbenes and exo/endo product selectivity for clarifying the mechanism of ring-closing enyne metathesis. J Org Chem (2013) 0.80

Confirmed case of encephalitis caused by Murray Valley encephalitis virus infection in a horse. J Vet Diagn Invest (2012) 0.80

Chemical control of yeast cell division by cross-linked shells of catechol-grafted polyelectrolyte multilayers. Macromol Rapid Commun (2013) 0.80

Anhydrous hydration of nitriles to amides using aldoximes as the water source. Org Lett (2009) 0.79

Synthesis of the C21-C34 fragment of antascomicin B. Tetrahedron Lett (2011) 0.79

Stereospecific mechanism of DJ-1 glyoxalases inferred from their hemithioacetal-containing crystal structures. FEBS J (2014) 0.79

New insights in the mechanism of amine catalyzed epoxidation: dual role of protonated ammonium salts as both phase transfer catalysts and activators of oxone. J Am Chem Soc (2003) 0.79

Total synthesis of panaginsene with structural revision. Org Lett (2014) 0.79

A new structural class of S-adenosylhomocysteine hydrolase inhibitors. Bioorg Med Chem (2009) 0.79

On the origin of high E selectivity in the Wittig reaction of stabilized ylides: importance of dipole-dipole interactions. J Am Chem Soc (2005) 0.78

Dengue virus infection in Australia following occupational exposure: a reflection of increasing numbers of imported cases. J Clin Virol (2012) 0.78

Structure-activity relationship studies of a series of novel delta-lactam-based histone deacetylase inhibitors. J Med Chem (2007) 0.78

A receptor-independent, cell-based JAK activation assay for screening for JAK3-specific inhibitors. J Immunol Methods (2010) 0.77

Phorbasones A and B, sesterterpenoids isolated from the marine sponge Phorbas sp. and induction of osteoblast differentiation. Org Lett (2011) 0.77

Gelastatins and their hydroxamates as dual functional inhibitors for TNF-alpha converting enzyme and matrix metalloproteinases: synthesis, biological evaluation, and mechanism studies. Biochem Biophys Res Commun (2006) 0.77

Virulence and Evolution of West Nile Virus, Australia, 1960-2012. Emerg Infect Dis (2016) 0.77

Sulfhydryl-specific probe for monitoring protein redox sensitivity. ACS Chem Biol (2014) 0.76

Total synthesis of (-)-crinipellin A. J Am Chem Soc (2014) 0.76

Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors. Bioorg Med Chem Lett (2010) 0.75

Idiopathic intracranial hypertension: The presence and morphology of sinovenous stenosis. Neurology (2004) 0.75

Cutaneous conditions leading to dermatology consultations in the emergency department. West J Emerg Med (2011) 0.75

Effect of sulfide structure on enantioselectivity in catalytic asymmetric epoxidation of aldehydes: mechanistic insights and implications. Proc Natl Acad Sci U S A (2004) 0.75

Characterization of Fitzroy River Virus and Serologic Evidence of Human and Animal Infection. Emerg Infect Dis (2017) 0.75

Dynamics and mechanism of flame retardants in polymer matrixes: experiment and simulation. J Phys Chem B (2013) 0.75

Influence of sticky trap color and height above ground on capture of alate Elatobium abietinum (Hemiptera: Aphididae) in Sitka spruce plantations. Environ Entomol (2011) 0.75

Total synthesis of ceratopicanol through tandem cycloaddition reaction of a linear substrate. Chem Asian J (2012) 0.75

Unexpected formation of a trans-syn-fused linear triquinane from a trimethylenemethane (TMM)-diyl-mediated [2+3] cycloaddition reaction. Chem Asian J (2011) 0.75

Immobilization of Antibody on a Cyclic Olefin Copolymer Surface with Functionalizable, Non-Biofouling Poly[Oligo(Ethylene Glycol) Methacrylate]. J Nanosci Nanotechnol (2015) 0.75

Novel Hendra Virus Variant Detected by Sentinel Surveillance of Horses in Australia. Emerg Infect Dis (2022) 0.75

Design and synthesis of a piperazinylalkylisoxazole library for subtype selective dopamine receptor ligands. Bioorg Med Chem Lett (2002) 0.75

Two-step cyanomethylation protocol: convenient access to functionalized aryl- and heteroarylacetonitriles. Org Lett (2015) 0.75

Conducting Polymer Coated Graphene Oxide Electrode for Rechargeable Lithium-Sulfur Batteries. J Nanosci Nanotechnol (2016) 0.75

Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening. Org Lett (2004) 0.75

Stereoselectivity in trimethylenemethane (TMM) diyl mediated cycloaddition reaction to angularly fused triquinanes. Chem Asian J (2010) 0.75