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Featured researches published by Tatsuya Shono.


Tetrahedron | 1972

Electroorganic chemistry—XI : The stereochemistry of electroreduction of cyclic ketones

Tatsuya Shono; M. Mitani

Abstract Cyclic ketones were electrolytically reduced in isopropanol and in H 2 SO 4 H 2 OMeOH. It was found that, in isopropanol the stereoisomer ratios of the products were approximately equal to the thermodynamic relative stabilities, whereas in H 2 SO 4 H 2 OMeOH the thermodynamically unstable epimeric alcohols formed were more than that anticipated from the relative stabilities. The mechanism of this electroreduction involving the stereoselective adsorption and electron transfer is discussed.


Tetrahedron Letters | 1980

Electroreductive hydrocoupling of activated olefins with ketones or aldehydes in the presence of trimethylchlorosilane

Tatsuya Shono; Hiroshi Ohmizu; Souta Kawakami; Hiroshi Sugiyama

Abstract Electroreductive crossed hydrocoupling of α,β-unsaturated esters with aldehydes or ketones in the presence of trimethylchlorosilane afforded γ-lactones in good yields. Similarly, α,β-unsaturated nitriles gave γ-hydroxynitriles in high yields.


Tetrahedron Letters | 1987

A new method for regioselective synthesis of 2-substituted 1-(methoxycarbonyl)-1,2-dihydropyridines☆

Tatsuya Shono; Yoshihiro Matsumura; Osamu Onomura; Yasufu Yamada

Abstract 2-Substituted 1,2-dihydropyridines including an optically active one were regioselectively prepared from 2-substituted piperidines through three intermediates, that is, (a) 1,2,3,4-tetrahydropyridines, (b) 5-bromo-6-methoxypiperidines, and (c) 1,2,3,6-tetrahydro- 6-methoxypyridines.


Tetrahedron Letters | 1983

Stereoselective synthesis of (±)-conhydrine, (±)-ephedrine, and (±)-N-methylephedrine

Tatsuya Shono; auYoshihiro Matsumura; Takenobu Kanazawa

Abstract (±)-Conhydrine, (±)-ephedrine, and (±)-N-methylephedrine have been synthesized with a complete stereochemical control by utilizig carbanions in which the negative charge is located at the position α to the nitrogen atom of N-acylamines.


Tetrahedron Letters | 1981

A new carbon—phosphorous bond forming reaction and synthesis of aminoalkylphosphonic acid derivatives☆

Tatsuya Shono; Yoshihiro Matsumura; Kenji Tsubata

Abstract A new carbon—phosphorous bond forming reaction, that is, the reaction of α-methoxyurethanes with trialkyl phosphites in the presence of Lewis acid catalysts was studied on twelve examples.


Tetrahedron Letters | 1980

Electrooxidation of alcohols using a new double mediatory system

Tatsuya Shono; Yoshihiro Matsumura; Jue Hayashi; Mikiko Mizoguchi

Abstract The electrochemical oxidation of alcohols was accomplished by using a double mediatory system in which both alkyl methyl sulfide and bromide act in concert as mediators.


Tetrahedron Letters | 1990

Electroreductive intramolecular coupling of γ- and δ-cyanoketones

Tatsuya Shono; Naoki Kise

Abstract Electroreduction of γ- and δ-cyanoketones in i-PrOH gave cyclized products α-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojasmone, methyl dihydrojasmonate, and Rosaprostol.


Tetrahedron Letters | 1981

A new synthetic method of α-amino acids from α-methoxyurethanes

Tatsuya Shono; Yoshihiro Matsumura; Kenji Tsubata

Abstract Reaction of α-methoxyurethanes with phenylisocyanide gave the corresponding amides of α-amino acid in reasonable yields.


Tetrahedron | 1974

Small ring compounds—XXX : Homolytical aromatic substitution and hydrogen abstraction reaction with cyclopropyl radical☆

Tatsuya Shono; I. Nishiguchi

Abstract Homolytic aromatic substitution and hydrogen abstraction reactions with cyclopropyl radical were carried out to determine the reactivity and ionic character of cyclopropyl radical by examination of the orientation effect, partial rate factor and influence of substituents. By thermal decomposition of biscyclopropaneformyl peroxide in a series of substituted benzenes, the corresponding cyclopropylated benzene derivatives (the mixture of ortho, meta and para isomers) were obtained in moderate yield. In view of the orientation effect and the partial rate factor, the cyclopropyl radical seems to be fairly free from polar effect, and to resemble the phenyl radical more than the common alkyl radical although the cyclopropyl radical has a slightly higher reactivity than the phenyl radical. The relative reactivity of the 2-phenylcyclopropyl radical in the hydrogen abstraction reaction toward the benzylic position of ring-substituted toluenes gave good Hammetts correlation with the slope of + 0·20 suggesting little ionic character in the transition state. This result was in good agreement with the conclusion obtained from homolytic aromatic substitution reaction and with the chemical reactivity to be expected from the non-planar nearly sp 2 -hybridized conformation of the cyclopropyl radical.


Journal of The Chemical Society, Chemical Communications | 1992

Electroreductive synthesis of polygermane and germane–silane copolymer

Tatsuya Shono; Shigenori Kashimura; Hiroaki Murase

Formation of Ge–Ge and Ge–Si bonds has been achieved by electroreduction with an Mg electrode and this method has been successfully applied to the preparation of polygermane and germane–silane copolymer.

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