Shinji Harada

ORCID: 0000-0003-4042-9744
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About
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Research Areas
  • Asymmetric Synthesis and Catalysis
  • Crystallization and Solubility Studies
  • X-ray Diffraction in Crystallography
  • Synthetic Organic Chemistry Methods
  • Catalytic C–H Functionalization Methods
  • Asymmetric Hydrogenation and Catalysis
  • Oxidative Organic Chemistry Reactions
  • Viral-associated cancers and disorders
  • Cyclopropane Reaction Mechanisms
  • T-cell and Retrovirus Studies
  • Synthesis and Catalytic Reactions
  • Crystallography and molecular interactions
  • Advanced Combustion Engine Technologies
  • Catalytic Cross-Coupling Reactions
  • Fluorine in Organic Chemistry
  • Microbial Natural Products and Biosynthesis
  • Radical Photochemical Reactions
  • Vector-Borne Animal Diseases
  • Chemical synthesis and alkaloids
  • Engineering Applied Research
  • Lymphoma Diagnosis and Treatment
  • Fungal Biology and Applications
  • Axial and Atropisomeric Chirality Synthesis
  • Coordination Chemistry and Organometallics
  • Immune Cell Function and Interaction

Chiba University
2015-2025

Osaka City University
2024

Osaka National Hospital
2024

Hokuto Hospital
2022

University of Bristol
2020

Korea University
2020

Pohang University of Science and Technology
2020

University of Ferrara
2020

Tokyo University of Pharmacy and Life Sciences
2020

Salisbury University
2020

An anti-selective direct catalytic asymmetric Mannich-type reaction is described. The Et2Zn/(S,S)-linked-BINOL 1 = 4/1 complex promoted a of 2-hydroxy-2‘-methoxyacetophenone (2) and N-diphenylphosphinoyl imines 3. Using as little 0.25−1 mol % the catalyst, we obtained Mannich adducts 4 in excellent yield (up to 99%), diastereoselectivity (anti/syn up >98/2), enantiomeric excess >99.5%). anti-selectivity present system complementary that observed using previously reported methods, providing...

10.1021/ja034787f article EN Journal of the American Chemical Society 2003-03-27

Full details of our newly developed catalyses with asymmetric zinc complexes as mimics class II zinc-containing aldolase are described. A Et(2)Zn/(S,S)-linked-BINOL complex was and successfully applied to direct catalytic aldol reactions hydroxyketones. 1 = 2/1 system initially developed, which efficiently promoted the reaction 2-hydroxy-2'-methoxyacetophenone (7d). Using mol % (S,S)-linked-BINOL 2 Et(2)Zn, we obtained 1,2-dihydroxyketones syn-selectively in high yield (up 95%), good...

10.1021/ja028926p article EN Journal of the American Chemical Society 2003-02-01

A silver-mediated cross-coupling of trifluoromethoxide with aryl stannanes and arylboronic acids to give trifluoromethyl ethers is reported. This the first report a transition-metal-mediated Caryl–OCF3 bond formation.

10.1021/ja204861a article EN Journal of the American Chemical Society 2011-08-09

Synthesis and application of α,β-unsaturated N-acylpyrroles as highly reactive, monodentate ester surrogates in the catalytic asymmetric epoxidation Michael reactions are described. α,β-Unsaturated with various functional groups were synthesized by Wittig reaction using ylide 2. A Sm(O-i-Pr)3/H8-BINOL complex was most effective catalyst for to afford pyrrolyl epoxides up 100% yield >99% ee. Catalyst loading successfully reduced little 0.02 mol % (substrate/catalyst = 5000). The high turnover...

10.1021/ja0485917 article EN Journal of the American Chemical Society 2004-05-26

Fexofenadine, a nonsedating, H1-receptor selective antihistamine, exhibits consistent efficacy and safety in the treatment of allergic rhinitis urticaria. The pruritus associated with atopic dermatitis is considered to be induced, part, by histamine. Therefore, we thought that fexofenadine may useful relief dermatitis.To compare twice-daily hydrochloride (HCl) 60 mg vs. placebo reducing dermatitis.In this randomized, multicentre, double-blind, placebo-controlled study, patients (aged >or= 16...

10.1046/j.1365-2133.2003.05293.x article EN British Journal of Dermatology 2003-06-01

Stretching the limits of Mannich reaction: A new indium–binol catalyst was used to generate enolate ester-equivalent donor in situ (see scheme). The donor, an N-acylpyrrole, has many similarities aromatic ketone, particular enolates should have same coordination mode. Versatile β-amino-α-hydroxy carboxylic acid derivatives were obtained high yield and ee values. Supporting information for this article is available on WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501180_s.pdf or...

10.1002/anie.200501180 article EN Angewandte Chemie International Edition 2005-06-07

A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La−Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions racemic nitroaldols. By using a mixture La−Li3−(1a)3 complex (LLB 2a) and La−Li3−(1b)3 (LLB* 2b) ratio 2/1, chiral were obtained 80−97% ee 30−47% recovery yield.

10.1021/ja064858l article EN Journal of the American Chemical Society 2006-08-19

Abstract Eleven males with XLP were evaluated for EBV-specific antibodies during periods of 2 to 7 yr. Variable responses antigens found. All 11 patients had subnormal anti-EBNA titers, which probably reflected a T cell deficiency. The showed four different patterns in their anti-VCA response: 1) two boys who experienced malignant lymphoma mounted no at all; 2) intermittent titers; 3) persistently elevated and 4) three normal titers. ADCC against EBV-infected cells was abnormally low six...

10.4049/jimmunol.129.6.2532 article EN The Journal of Immunology 1982-12-01

The catalytic and asymmetric cycloaddition between 3-[1-(silyloxy)vinyl]indoles electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct tricyclic compound with four continuous centers, one which quaternary carbon.

10.1021/ol402559z article EN Organic Letters 2013-09-30

1-Methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky's diene) is recognized as a synthetically useful diene due to its high reactivity in the Diels−Alder reaction with electron-deficient alkenes give oxygen-functionalyzed cyclohexenes and substituted cyclohexenones, which are important building blocks for total synthesis of natural products. However, development catalytic enantioselective versions reactions using Danishefsky type dienes has been difficult because instability under Lewis...

10.1021/ja804430n article EN Journal of the American Chemical Society 2008-08-30

Chemical transformers! Catalytic nucleophilic activation of trichloromethyl ketones allows applications in intermolecular carbon–carbon bond-forming reactions. Mannich adducts such as azetidines can be obtained from the primary products high yield and syn selectivity. PG=protecting group. Supporting information for this article is available on WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z600227_s.pdf or author. Please note: The publisher not responsible content functionality any...

10.1002/anie.200600227 article EN Angewandte Chemie International Edition 2006-04-05

The objective of this study is to find strategies for extending the load range premixed charge compression ignition-based combustion while improving thermal efficiency and reducing noise exhaust emission levels. Experiments were performed using a single-cylinder direct-injection diesel engine equipped with common-rail injection system cooled EGR system. First, experiments carried out single-stage injection. results indicated notable improvement NO x smoke emissions by selecting lower rates...

10.1243/14680874jer02709 article EN International Journal of Engine Research 2009-04-01

A Ni(NTf2)2 and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture Ni substrate, which dinuclear chiral complex. From information regarding structure complex, substrate distorted to form helical shape, carbon atoms involved in bond formation were close each other. In addition, mechanistic studies revealed that configuration olefin moiety isomerized before formation.

10.1021/acs.orglett.5b02497 article EN Organic Letters 2015-10-14

A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)3 as a Lewis acidic reagent. This method demonstrates broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, provides versatile route to complex nitrogen-containing scaffolds potential applications in medicinal chemistry total synthesis biologically...

10.1021/acs.orglett.5c00125 article EN Organic Letters 2025-02-04

Abstract. We propose a new method to rid solutions of virus by using novel regenerated multilayered structured cellulose membrane (BMM). When the filtrate human immunodeficiency (HIV) preparation was obtained through BMM it showed no infectivity. Electron microscopic observation revealed that HIV completely caught multilayers BMM. Conveniently, seldomly found adsorb protein molecules and also have high filtration rate. These characteristics may use in removal other variously sized pathogenic...

10.1111/j.1423-0410.1989.tb02034.x article EN Vox Sanguinis 1989-05-01

Full details of our direct Michael addition unmodified ketones using new asymmetric zinc catalysis are described. Et(2)Zn/(S,S)-linked-BINOL complexes were successfully applied to 1,4-addition reactions hydroxyketones. The first generation 1 = 2/1 system was effective for 2-hydroxy-2'-methoxyacetophenone (3). Using mol % (S,S)-linked-BINOL and 2 Et(2)Zn, we found that a reaction beta-unsubstituted enone proceeded smoothly at 4 degrees C afford products in high yield (up 90%) enantiomeric...

10.1021/ja028928+ article EN Journal of the American Chemical Society 2003-02-04

Abstract Previously, we reported that cells of the human T‐cell lymphotropic virus type 1 (HTLV‐I)‐transformed lines MT‐2 and MT‐4 were extensively killed by infection with AIDS retrovirus HTLY‐III. We have investigated this phenomenon more systematically using light electron microscopy as well immunofluorescence. The cell used in present studies included 14 those carrying not only HTLY‐1 but also related simian agents 6 HTLY‐I‐negative T‐ B‐cell lines. results showed cytocidal effects...

10.1002/ijc.2910360406 article EN International Journal of Cancer 1985-10-15

Indium(III)-catalyzed asymmetric alkynylation of aryl, heteroaryl, alkyl and alkenyl aldehydes with 2-methyl-3-butyn-2-ol as an ethyne equivalent donor was realized, products were obtained in moderate to good yields (up 97%) high enantioselectivities 99% ee) using 2-10 mol% catalyst.

10.1039/b614958h article EN Chemical Communications 2006-12-01

The catalytic and enantioselective total synthesis of (-)-minovincine has been accomplished. key highly substituted hydrocarbazole derivative was obtained by an asymmetric Diels-Alder reaction siloxyvinylindole catalyzed 0.5 mol % a chiral holmium complex. adduct converted to tetracyclic intermediate in one-pot procedure. No waste stereoisomers were produced throughout the entire synthesis.

10.1021/acs.joc.5b01393 article EN The Journal of Organic Chemistry 2015-08-06
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