(S)-selective kinetic resolution and chemoenzymatic dynamic kinetic resolution of secondary alcohols.

PubWeight™: 0.95‹?› | Rank: Top 15%

🔗 View Article (PMID 16267860)

Published in Chemistry on December 16, 2005

Authors

Linnéa Borén1, Belén Martín-Matute, Yongmei Xu, Armando Córdova, Jan-E Bäckvall

Author Affiliations

1: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.

Articles by these authors

Chemoenzymatic design of heparan sulfate oligosaccharides. J Biol Chem (2010) 1.64

Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions. Chem Soc Rev (2006) 1.38

Catalytic oxidation of organic substrates by molecular oxygen and hydrogen peroxide by multistep electron transfer--a biomimetic approach. Angew Chem Int Ed Engl (2008) 1.32

Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions. Chemistry (2010) 1.22

Direct catalytic enantioselective aza-Diels-Alder reactions. Angew Chem Int Ed Engl (2005) 1.19

Combination of enzymes and metal catalysts. A powerful approach in asymmetric catalysis. Chem Rev (2003) 1.14

Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions. J Am Chem Soc (2006) 1.13

Dissecting the substrate recognition of 3-O-sulfotransferase for the biosynthesis of anticoagulant heparin. Proc Natl Acad Sci U S A (2012) 1.11

Organocatalytic enantioselective aminosulfenylation of alpha,beta-unsaturated aldehydes. Angew Chem Int Ed Engl (2008) 1.08

The dominating role of N-deacetylase/N-sulfotransferase 1 in forming domain structures in heparan sulfate. J Biol Chem (2011) 1.06

Uncovering biphasic catalytic mode of C5-epimerase in heparan sulfate biosynthesis. J Biol Chem (2012) 1.05

Toward an artificial Golgi: redesigning the biological activities of heparan sulfate on a digital microfluidic chip. J Am Chem Soc (2009) 1.04

X-ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation. J Mol Biol (2007) 1.01

Direct catalytic intermolecular alpha-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis. Angew Chem Int Ed Engl (2006) 1.01

Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism. J Am Chem Soc (2005) 1.01

Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids. Chem Commun (Camb) (2006) 1.01

Enantioselective alpha-hydroxylation of 2-arylacetic acid derivatives and buspirone catalyzed by engineered cytochrome P450 BM-3. J Am Chem Soc (2006) 1.00

Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides. Chemistry (2006) 0.98

Palladium(II)-catalyzed oxidative carbocyclization of aza-enallenes. Angew Chem Int Ed Engl (2010) 0.95

Combinatorial reshaping of the Candida antarctica lipase A substrate pocket for enantioselectivity using an extremely condensed library. Proc Natl Acad Sci U S A (2011) 0.95

Direct amino acid catalyzed asymmetric synthesis of polyketide sugars. Angew Chem Int Ed Engl (2005) 0.94

Molecular mechanism of substrate specificity for heparan sulfate 2-O-sulfotransferase. J Biol Chem (2014) 0.94

Catalytic enantioselective domino oxa-michael/aldol condensations: asymmetric synthesis of benzopyran derivatives. Chemistry (2007) 0.94

Photosensitized water oxidation by use of a bioinspired manganese catalyst. Angew Chem Int Ed Engl (2011) 0.93

Palladium-catalyzed oxidative borylative carbocyclization of enallenes. Angew Chem Int Ed Engl (2011) 0.93

Structurally informative tandem mass spectrometry of highly sulfated natural and chemoenzymatically synthesized heparin and heparan sulfate glycosaminoglycans. Mol Cell Proteomics (2013) 0.92

Enantioselective organocatalytic hydrophosphination of alpha,beta-unsaturated aldehydes. Angew Chem Int Ed Engl (2007) 0.92

One-pot three-component catalytic enantioselective synthesis of homoallylboronates. Angew Chem Int Ed Engl (2011) 0.92

Dynamic kinetic resolution catalyzed by enzymes and metals. Curr Opin Chem Biol (2007) 0.90

Highly efficient synthesis of enantiopure diacetylated C(2)-symmetric diols by ruthenium- and enzyme-catalyzed dynamic kinetic asymmetric transformation (DYKAT). Chemistry (2006) 0.90

Directed evolution of an enantioselective lipase with broad substrate scope for hydrolysis of alpha-substituted esters. J Am Chem Soc (2010) 0.90

Direct amino acid catalyzed asymmetric alpha oxidation of ketones with molecular oxygen. Angew Chem Int Ed Engl (2004) 0.89

Palladium-catalyzed oxidative arylating carbocyclization of allenynes. Angew Chem Int Ed Engl (2012) 0.89

Probing structural selectivity of synthetic heparin binding to Stabilin protein receptors. J Biol Chem (2012) 0.89

Control of selectivity in palladium-catalyzed oxidative carbocyclization/borylation of allenynes. Angew Chem Int Ed Engl (2013) 0.89

Efficient ruthenium-catalyzed transfer hydrogenation/hydrogenation of 1,3-cycloalkanediones to 1,3-cycloalkanediols using microwave heating. J Org Chem (2006) 0.89

Water as nucleophile in palladium-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes. J Am Chem Soc (2007) 0.89

Direct catalytic enantioselective alpha-aminoxylation of ketones: a stereoselective synthesis of alpha-hydroxy and alpha,alpha'-dihydroxy ketones. Angew Chem Int Ed Engl (2004) 0.89

Simple highly modular acyclic amine-catalyzed direct enantioselective addition of ketones to nitro-olefins. Chem Commun (Camb) (2006) 0.89

One-pot catalytic enantioselective domino nitro-michael/michael synthesis of cyclopentanes with four stereocenters. Chemistry (2008) 0.88

PdII-catalyzed aerobic allylic oxidative carbocyclization of allene-substituted olefins: immobilization of an oxygen-activating catalyst. Angew Chem Int Ed Engl (2006) 0.88

Inorganic ammonium salts and carbonate salts are efficient catalysts for aldol condensation in atmospheric aerosols. Phys Chem Chem Phys (2010) 0.88

Palladium-catalyzed oxidative carbocyclizations. Chemistry (2012) 0.88

Therapeutic hypercapnia improves functional recovery and attenuates injury via antiapoptotic mechanisms in a rat focal cerebral ischemia/reperfusion model. Brain Res (2013) 0.88

Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution. J Org Chem (2010) 0.87

Mechanistic study of hydrogen transfer to imines from a hydroxycyclopentadienyl ruthenium hydride. Experimental support for a mechanism involving coordination of imine to ruthenium prior to hydrogen transfer. J Am Chem Soc (2006) 0.87

Carbon-carbon bond formation in palladium(II)-catalyzed allylic oxidation: a novel oxidative carbocyclization of allene-substituted olefins. J Am Chem Soc (2003) 0.87

The small peptide-catalyzed direct asymmetric aldol reaction in water. Org Biomol Chem (2005) 0.87

Organocatalytic enantioselective aziridination of alpha,beta-unsaturated aldehydes. Angew Chem Int Ed Engl (2007) 0.87

Efficient ruthenium-catalyzed aerobic oxidation of alcohols using a biomimetic coupled catalytic system. J Org Chem (2002) 0.86

Copper-catalyzed N-allenylation of allylic sulfonamides. Org Lett (2009) 0.86

The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes. Chemistry (2014) 0.85

Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes. Angew Chem Int Ed Engl (2015) 0.85

Highly compatible metal and enzyme catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature. Angew Chem Int Ed Engl (2004) 0.85

Highly dispersed palladium nanoparticles on mesocellular foam: an efficient and recyclable heterogeneous catalyst for alcohol oxidation. Chemistry (2012) 0.85

Chemoenzymatic dynamic kinetic resolution of axially chiral allenes. Chemistry (2010) 0.85

Palladium-catalyzed oxidative carbocyclization/arylation of enallenes. Org Lett (2011) 0.84

Direct catalytic enantioselective alpha-aminomethylation of ketones. Angew Chem Int Ed Engl (2004) 0.84

Mechanism of hydrogen transfer to imines from a hydroxycyclopentadienyl ruthenium hydride. Support for a stepwise mechanism. Chem Commun (Camb) (2004) 0.84

An enantioselective route to alpha-methyl carboxylic acids via metal and enzyme catalysis. Org Lett (2007) 0.84

Dynamic kinetic asymmetric transformation (DYKAT) by combined amine- and transition-metal-catalyzed enantioselective cycloisomerization. Chemistry (2010) 0.84

Mechanisms and kinetics for sorption of CO2 on bicontinuous mesoporous silica modified with n-propylamine. Langmuir (2011) 0.84

Risk for postpartum depression, breastfeeding practices, and mammary gland permeability. J Hum Lact (2008) 0.83

Small Pd nanoparticles supported in large pores of mesocellular foam: an excellent catalyst for racemization of amines. Chemistry (2011) 0.83

Allenes as carbon nucleophiles in intramolecular attack on (pi-1,3-diene)palladium complexes: evidence for trans carbopalladation of the 1,3-diene. Chemistry (2003) 0.83

Dynamic processes in the copper-catalyzed substitution of chiral allylic acetates leading to loss of chiral information. Chemistry (2007) 0.83

Organocatalytic enantioselective conjugate addition of aldehydes to maleimides. Chem Commun (Camb) (2007) 0.83

Chemoenzymatic dynamic kinetic resolution of beta-halo alcohols. An efficient route to chiral epoxides. J Org Chem (2002) 0.83

A chemoenzymatic approach to enantiomerically pure amines using dynamic kinetic resolution: application to the synthesis of norsertraline. Chemistry (2009) 0.83

Efficient ruthenium-catalyzed aerobic oxidation of amines by using a biomimetic coupled catalytic system. Chemistry (2005) 0.83

Chemoenzymatic dynamic kinetic resolution. Trends Biotechnol (2004) 0.83

Dehydrogenation of aromatic amines to imines via ruthenium-catalyzed hydrogen transfer. Chem Commun (Camb) (2002) 0.83

Direct catalytic asymmetric anti-selective Mannich-type reactions. Chem Commun (Camb) (2006) 0.82

N-sulfotestosteronan, a novel substrate for heparan sulfate 6-o-sulfotransferases and its analysis by oxidative degradation. Biopolymers (2013) 0.82

Aerobic lactonization of diols by biomimetic oxidation. Chemistry (2011) 0.82

Palladium-catalyzed oxidative acyloxylation/carbocyclization of allenynes. Angew Chem Int Ed Engl (2013) 0.82

One-pot organocatalytic domino Michael/alpha-alkylation reactions: direct catalytic enantioselective cyclopropanation and cyclopentanation reactions. Chemistry (2008) 0.82

Palladium-catalyzed aerobic domino oxidative carbocyclization-alkynylation of allenynes. Angew Chem Int Ed Engl (2013) 0.82

Palladium-catalyzed oxidative arylating carbocyclization of allenynes: control of selectivity and role of H₂O. Angew Chem Int Ed Engl (2014) 0.82

Enantioselective synthesis of syn- and anti-1,3-aminoalcohols via β-aminoketones and subsequent reduction/dynamic kinetic asymmetric transformation. J Am Chem Soc (2010) 0.82

Influence of delta-functional groups on the enantiorecognition of secondary alcohols by Candida antarctica lipase B. Chembiochem (2008) 0.81

Fibroblast growth factor-based signaling through synthetic heparan sulfate blocks copolymers studied using high cell density three-dimensional cell printing. J Biol Chem (2014) 0.81

Palladium(II)-catalyzed oxidative cyclization of allylic tosylcarbamates: scope, derivatization, and mechanistic aspects. Chemistry (2012) 0.81

Gold-catalyzed cyclization of allene-substituted malonate esters: synthesis of beta,gamma-unsaturated delta-lactones. Org Lett (2007) 0.81

Efficient synthesis of beta-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates. Chemistry (2008) 0.81

Palladium-catalyzed oxidative diarylating carbocyclization of enynes. Org Lett (2012) 0.81

Palladium-catalyzed oxidative carbocyclization-carbonylation of allenynes and enallenes. Chemistry (2014) 0.81

Ir-catalysed formation of C-F bonds. From allylic alcohols to α-fluoroketones. Chem Commun (Camb) (2011) 0.81

Small peptides as modular catalysts for the direct asymmetric aldol reaction: ancient peptides with aldolase enzyme activity. Chem Commun (Camb) (2005) 0.81

Dynamic kinetic asymmetric domino oxa-Michael/carbocyclization by combination of transition-metal and amine catalysis: catalytic enantioselective synthesis of dihydrofurans. Chemistry (2010) 0.81

Products and kinetics of the liquid-phase reaction of glyoxal catalyzed by ammonium ions (NH4(+)). J Phys Chem A (2009) 0.81

Aerobic double dehydrogenative cross coupling between cyclic saturated ketones and simple arenes. Chemistry (2014) 0.80

An efficient route to chiral alpha- and beta-hydroxyalkanephosphonates. J Org Chem (2003) 0.80

Mechanism of the palladium-catalyzed carbohydroxylation of allene-substituted conjugated dienes: rationalization of the recently observed nucleophilic attack by water on a (pi-allyl)palladium intermediate. Chemistry (2008) 0.80

Efficient reoxidation of palladium by a hybrid catalyst in aerobic palladium-catalyzed carbocyclization of enallenes. Chemistry (2009) 0.80

Cycloisomerization of acetylenic acids to γ-alkylidene lactones using a palladium(II) catalyst supported on amino-functionalized siliceous mesocellular foam. J Org Chem (2014) 0.80

Asymmetric synthesis of bicyclic diol derivatives through metal and enzyme catalysis: application to the formal synthesis of sertraline. Chemistry (2010) 0.80

Enantioselective enzymatic desymmetrization of prochiral allenic diols. Angew Chem Int Ed Engl (2011) 0.80