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en: 5-exo-Selective Asymmetric Bromolactonization of Stilbenecarboxylic Acids Catalyzed by Phenol-bearing Chiral Thiourea

en: We developed a novel thiourea Lewis-base catalyst with phenol moieties for the enantioselective 5--bromolactonization of stilbenecarboxylic acids to afford chiral 3-substituted phthalides. The phenol moieties are crucial for the enantio- and regio-selectivity.

en: Organic & Biomolecular Chemistry

ja: Organic & Biomolecular Chemistry


en: Evaluation of Quantum Chemistry Calculation Methods for Conformational Analysis of Organic Molecules Using A-Value Estimation as a Benchmark Test.

en: A-values of 20 substituents were estimated by quantum chemistry calculations of different theoretical levels. Comparison with the reported experimental values provided a good benchmark to evaluate the theoretical levels for the conformational analysis of organic molecules.

en: RSC Advances

ja: RSC Advances


en: Efficient Synthesis of Medium-sized Nitrogen Heterocycles by Brønsted Acid-Catalyzed Cyclization of Ene-ynamides

en: Asian Journal of Organic Chemistry

ja: Asian Journal of Organic Chemistry


en: Remote Electronic Effect of Chiral N-Heterocyclic Carbene Catalyst on an Asymmetric Benzoin Reaction

en: A remote electronic effect of chiral aminoindanol-derived N-heterocyclic carbene catalyst on an asymmetric benzoin reaction was investigated. The catalyst bearing remote electron-withdrawing substituents increased enantioselectivity of the reaction at the cost of the reaction rate. DFT calculations rationalized the increased enantioselectivity.

en: Chemistry - A European Journal

ja: Chemistry - A European Journal


en: Remote electronic effect on the N-heterocyclic carbene-catalyzed asymmetric intramolecular Stetter reaction and structural revision of products

en: Chemical Communications

ja: Chemical Communications


en: Catalytic and Aerobic Oxidative C-H Annulation Reaction of Saturated Cyclic Amines for Synthesis of Dipyrroloquinolines

en: Advanced Synthesis & Catalysis

ja: Advanced Synthesis & Catalysis


en: Preparation of N-2-Nitrophenylsulfenyl Imino Peptides and Their Catalyst-Controlled Diastereoselective Indolylation

en: N-2-Nitrophenylsulfenyl (Nps) imino dipeptides bearing various functional groups were successfully prepared via MnO2mediated oxidation and then subjected to diastereoselective indolylation. Each diastereomer of the adduct was selectively obtained from the same substrates using the appropriate chiral phosphoric acid catalysts. These transformations would be useful for synthesizing non-canonical amino acid-containing peptides as novel drug candidates.


en: Kinetic Resolution of α-Hydroxyamide via N-Heterocyclic Carbene-Catalyzed Acylation


en: Lewis Acid-Catalyzed Diastereoselective Domino Reaction of Ene-Ynamide with Trimethylsilyl Cyanide to Construct Spiroindolines

en: The Zn(OTf)-catalyzed domino reaction of enamide-ynamides in the presence of trimethylsilyl cyanide as an external nucleophile to construct spirocyclic indolines was developed. This domino reaction involved cyclization of enamide to ynamide to generate 4',5'-dihydrospiro[indoline-3,3'-pyrrol]-1'-ium followed by cyanide addition to produce spiroindolopyrrolidines with good diastereoselectivity.

en: Organic Letters

ja: Organic Letters


en: Enhanced Molecular Recognition through SubstrateAdditive Complex Formation in N-Heterocyclic-Carbene-Catalyzed Kinetic Resolution of alpha-Hydroxythioamides.

en: ACS Catalysis

ja: ACS Catalysis


en: The Rationale for Stereoinduction in Conjugate Addition to Alkylidenemalonates Bearing a Menthol-derived Chiral Auxiliary

en: Tetrahedron

ja: Tetrahedron


en: Mechanistic Support for Intramolecular Migrative Cyclization of Propargyl Sulfones Provided by Catalytic Asymmetric Induction with a Chiral Counter Cation Strategy

en: Asian Journal of Organic Chemistry


en: Helical Nanographenes Embedded with Contiguous Azulene Units

en: Journal of the American Chemical Society


en: Cloning and Expression of a Perilla frutescens Cytochrome P450 Enzyme Catalyzing the Hydroxylation of Phenylpropenes

en: Plants

ja: Plants


en: Asymmetric Synthesis of α-Amino Phosphonic Acids Using Stable Imino Phosphonate as a Universal Precursor

en: Chemistry - A European Journal


en: Total Syntheses of Allelopathic 4-Oxyprotoilludanes, Melleolides, and Echinocidins

en: Stereocontrolled total syntheses of allelopathic 4-oxyprotoilludane sesquiterpenes, melleolide, melleolide F, and echinocidins B and D were achieved. The curved 5/6/4 tricyclic system with an angular hydroxy group was built via three key transformations: (1) MeAl-catalyzed [2 + 2] cycloaddition of a ketene silyl acetal with a propiolate, (2) reductive ring-opening of a cyclic hemiketal, and (3) the intramolecular Morita-Baylis-Hillman reaction. This synthetic route represents a new and reliable strategy to obtain protoilludanes with several oxy-functional groups.

en: The Journal of Organic Chemistry

ja: The Journal of Organic Chemistry


en: Synthesis of Functionalized MediumSized transCycloalkenes by 4π Electrocyclic Ring OpeningAlkylation Cascade

en: Angewandte Chemie International Edition

ja: Angewandte Chemie International Edition


en: Rapid Assembly of Protoilludane Skeleton through Tandem Catalysis: Total Synthesis of Paesslerin A and Its Structural Revision.

en: A multicomponent domino reaction involving three mechanistically distinct TfNH-catalyzed reactions was developed. The reaction cascade enables the assembly of a skewed 5/6/4 tricyclic motif with migration of the reactive site with the assistance of a catalyst. The tricyclic product was used to achieve the first total synthesis of cytotoxic paesslerin A by regioselective C-H insertion of the sulfonyl carbenoid and base-promoted olefin isomerization. Our results led to the revision of the originally proposed tricyclic structure of paesslerin A.

en: Organic Letters


en: Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine

en: Although (+)-catharanthine is an attractive alkaloid for both clinical research and organic synthetic chemistry, only a limited number of approaches for its catalytic asymmetric synthesis exist. Herein, we describe a novel strategy for synthesizing a chiral intermediate of (+)-catharanthine via phosphoric acid-catalyzed asymmetric desymmetrization of a meso-isoquinuclidine possessing a 1,3-diol unit that was synthesized by a formal amide insertion reaction.


en: Optical Resolution via Catalytic Generation of Chiral Auxiliary

en: Tetrahedron Letters

ja: Tetrahedron Letters


en: Aminolithiation-Arylation Consecutive Cyclization of N-(2-Fluorophenyl)methyl-aminoalkylstyryls Giving Aryl-substituted Pyrido[1,2-b]isoquinoline.

en: Tetrahedron


en: A recyclable hydrophobic anchor-tagged asymmetric amino thiourea catalyst

en: ChemCatChem

ja: ChemCatChem


en: Direct enantioselective indolylation of peptidyl imine for the synthesis of indolyl glycine-containing peptides

en: Heterocycles

ja: Heterocycles


en: TOTAL SYNTHESIS OF PHENANTHROQUINOLIZIDINE ALKALOID CRYPTOPLEURINE AND PHENANTHROINDOLIZIDINE ALKALOID TYLOPHORINE


en: Consecutive Aminolithiation Carbolithiation of a Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety to Give Hydro indolizine

en: Synlett

ja: Synlett


en: Synthesis of π-Extended Fluoranthenes via a KHMDS-promoted Anionic-Radical Reaction Cascade.

en: An unprecedented KHMDS-promoted domino reaction to furnish hydroxyfluoranthenes is described. Biaryl compounds bearing acyl and naphthylalkenyl moieties are transformed into 9-hydroxydibenzo[j,l]fluoranthenes in a single step through the formation of an aromatic and a pentagonal ring system. A variety of fluoranthenes including those with extended π-conjugation, a heteroaromatic ring, and unsymmetrical substituents could be synthesized. Mechanistic studies reveal a unique reaction cascade where KHMDS acts as both a base and a single-electron donor.


en: Synthesis of Multi-Substituted Cyclobutenes: Cyclic Strategy for [2+2] Cycloadditon of Ketene Silyl Acetals with Propiolates.


en: Synthesis and Biological Evaluation of Steroidal Derivatives Bearing a Small Ring as Vitamin D Receptor Agonists.

en: A novel series of 3-ketolithocholic acid derivatives as well as estrone derivatives bearing a small ring for the conformational fixation of the side chain were synthesized by using a catalytic [2+2] cycloaddition and a ring-contraction rearrangement. The steroidal derivatives were evaluated for transcriptional activation of vitamin D receptor by luciferase reporter assays. Among them, two estrone derivatives showed a higher efficacy of the transactivation of vitamin D receptor than 3-ketolithocholic acid, and the small ring moieties were found to be important for the efficacy.

en: Bioorganic & Medicinal Chemistry Letters


en: Site-selective Benzoin-type Cyclization of Unsymmetrical Dialdoses Catalyzed by N-Heterocyclic Carbenes for Divergent Cyclitol Synthesis.

en: A highly site-selective N-heterocyclic carbene (NHC)-catalyzed benzoin-type cyclization of unsymmetrical dialdoses is developed to enable a divergent cyclitol synthesis. The choice of chiral NHCs and protecting groups affects the site-selectivity. The resulting inososes are converted into epi-, muco- and myo-inositols, and their chiral protected derivatives are formed in good yields.

en: Chemical Communications


en: Phosphine-Promoted Migrative Cyclization of Sulfonylalkynol and Sulfonylalkynamide for the Synthesis of Oxa- and Azacycles.


en: Use of a Catalytic Chiral Leaving Group for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms: Kinetic Resolution of beta-Amino Alcohols by p-Methoxybenzylation .

en: Angewandte Chemie International Edition


en: Desymmetrization of Acid Anhydride with Asymmetric Esterification Catalyzed by Chiral Phosphoric Acid.

en: Tetrahedron Letters


en: Striking Difference between Succinimidomethyl and Phthalimidomethyl Radicals in Conjugate Addition to Alkylidenemalonate Initiated by Dimethylzinc.

en: We used dimethylzinc to develop a conjugate addition reaction of imidomethyl radicals to alkylidenemalonates, in which we observed a significant difference between succinimidomethyl and phthalimidomethyl radicals. This reaction provides new access to γ-aminobutyric acid derivatives, which often function as neurotransmitters.

en: The Journal of Organic Chemistry


en: Oxa- and Azacycle-formation via Migrative Cyclization of Sulfonylalkynol and Sulfonylalkynamide with N-Heterocyclic Carbene.

en: An N-heterocyclic carbene promotes cyclization of sulfonylalkynols and sulfonylalkynamides that accompanies 1,2-migration of the sulfonyl groups. This reaction provides a novel access to oxa- and azacycles possessing a pendent vinyl sulfone functionality, which, in turn, is amenable for further transformations.


en: Exploration of Dimethylzinc-Mediated Radical Reactions.

en: In this account, our studies on radical reactions that are promoted by dimethylzinc and air are described. Advantages of this reagent and differences from conventional radical initiators, such as triethylborane, are discussed.

en: Chemical Record

ja: Chemical Record


en: An Arylative Ring Expansion Cascade of Fused Cyclobutenes via Short-Lived Intermediates with Planar Chirality.

en: An arylative ring expansion cascade has been developed for the synthesis of medium-sized carbocycles from fused cyclobutenes. This reaction proceeds through a short-lived cis,trans-cycloalkadiene intermediate that is formed by thermal 4ϖ electrocyclic ring opening. Chirality transfer experiments provide direct evidence for the transient generation of the intermediate.

en: Journal of the American Chemical Society


en: Asymmetric Total Synthesis of Tylophorine via a Formal [2+2] Cycloaddition Followed by Migrative Ring Opening of a Cyclobutane.

en: Synthesis

ja: Synthesis


en: Organocatalytic Activation of the Leaving Group in the Intramolecular Asymmetric SN 2' Reaction.

en: A Brønsted-acid-catalyzed intramolecular enantioselective SN 2' reaction was developed utilizing trichloroacetimidate as a leaving group. The findings indicated that dual activation of the substrates is operative. This metal-free allylic alkylation allows highly enantioselective access to 2-vinylpyrrolidines bearing various substituents.


en: Cyclic Model for the Asymmetric Conjugate Addition of Organolithium with Enoate.


en: A Short Synthesis of (+)-β-Lycorane by Asymmetric Conjugate Addition Cascade.

en: Tetrahedron


en: Hydrostannylation-Cross-Coupling Strategy for Stereoselective Synthesis of Alkylidenemalonates and Related α,β-Unsaturated Esters.

en: European Journal of Organic Chemistry

ja: European Journal of Organic Chemistry


en: N-Heterocyclic Carbene-Catalyzed Benzoin Strategy for Divergent Synthesis of Cyclitol Derivatives from Alditols.

en: Advanced Synthesis & Catalysis


en: Synthesis of Steroidal Derivatives Bearing a Small Ring Using a Catalytic [2+2] Cycloaddition and a Ring-Contraction Rearrangement.


en: Contiguous Radical Pivaloyloxymethylation-Directed C(sp3)-H Iodination of N-Tosyl Cycloalkanecarbaldimine.

en: Tetrahedron Letters