研究者詳細 - 岡内　辰夫

論文 - 岡内　辰夫

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Synthetic Utilization of α-Phosphonovinyl Anions 査読有り

岡内　辰夫

Phosphorus, Sulfur and Silicon 144-146 689 - 692 1999年04月

Discovery of Novel Antitumor Sulfonamides Targeting G1 Phase of the Cell Cycle 査読有り

岡内　辰夫

Journal of Medicinal Chemistry 42 ( 19 ) 3789 - 3799 1999年04月

Vinylic C-F Bond Activation : Generation and Cross-Coupling Reactions of 1-Fluorovinylzirconocene 査読有り

岡内　辰夫

Tetrahedron Letters 40 ( 40 ) 7261 - 7265 1999年04月

A Facile Synthesis of 1-H-2, 2-Difluorovinylphosphorus Compounds from 2, 2, 2-Trifluoroethyl Trifluoromethanesulfonate and Substitutions of Their Vinylic Fluorines 査読有り

岡内　辰夫

Journal of Fluorine Chemistry 97 ( 1-2 ) 109 - 114 1999年04月

Synthetic utilization of α-phosphonovinyl anions 査読有り

Minami T., Kouno R., Okauchi T., Nakamura M., Ichikawa J.

Phosphorus, Sulfur and Silicon and Related Elements 144-146 689 - 692 1999年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

The α-phosphonovinyl anions, generated in situ from treatment of β-hetero-substituted vinylphosphonates 1a-c with LDA (or LTMP), were trapped with various electrophiles such as chlorotriorganosilanes, chlorotrimethylgermane, chlorotriorganotins, dimethyl disulfide, and halogen to afford the corresponding β-hetero-substituted α-functionalized vinylphosphonates 2-14 in good to excellent yields. The Friedel-Crafts reaction of α-(silyl) or α-(germyl)phosphonoketene dithioacetals 2, 9 or 4 with acid chlorides gave α-acylated phosphonoketene dithioacetals 15-19 in 53-91 % yields. The palladium-catalyzed cross-coupling reaction of β-ethoxy-α-(tributylstannyl)vinylphosphonate 13 with a variety of organic halides (R = acyl, allyl, aryl etc.) provided β-ethoxy-α-substituted vinylphosphonates 20-25 in good to moderate yields. The palladium-mediated cross-coupling reaction of α-(iodo)-vinylphosphonates 7, 14 with terminal acetylenes afforded α-alkynylated vinylphosphonates 26-29 in 69-83 % yields.

DOI： 10.1080/10426509908546338

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Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents 査読有り

Kouno R., Okauchi T., Nakamura M., Ichikawa J., Minami T.

Journal of Organic Chemistry 63 ( 18 ) 6239 - 6246 1998年09月

記述言語：英語掲載種別：研究論文（学術雑誌）

The β-hetero-substituted vinylphosphonates la-c on treatment with LDA or LTMP were readily lithiated at the α-position of the phosphono group, and the resulting α-lithiovinylphosphonates were trapped with various electrophiles to afford the corresponding α-functionalized vinylphosphonates 2-14 in 55-96% yields. The Friedel-Crafts reaction of α-(silyl)- or a-(germyl)-phosphonoketene dithioacetals 2, 9, or 4 with acid chlorides gave α-acylated phosphonoketene dithioacetals 15-19 in 53-91% yields. The palladium-catalyzed cross-coupling reaction of β-ethoxy-α-(tributylstannyl)vinylphosphonate 13 with a variety of organic halides (R = acyl, allyl, aryl, etc.) provided β-ethoxy-α-substituted vinylphosphonates 21-26 in good to moderate yields. The palladium-mediated cross-coupling reaction of α-(iodo)vinylphosphonates 7 and 14 with terminal acetylenes afforded α-alkynylated vinylphosphonates 41-44 in 69-83% yields. Several α-functionalized β-hetero-substituted vinylphosphonates were applied to the synthesis of pyrazoles and an isoxazole possessing a phosphono function.

DOI： 10.1021/jo980467g

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Fluorine-directed Nazarov cyclizations 2: Regioselective synthesis of 5-trifluoromethyl-2-Cyclopentenones 査読有り

Ichikawa J., Fujiwara M., Okauchi T., Minami T.

Synlett ( 8 ) 927 - 929 1998年08月

記述言語：英語掲載種別：研究論文（学術雑誌）

1-Trifluoromethylvinyl vinyl ketones are treated with trimethylsilyl trifluoromethanesulfonate in CH 2 Cl 2 -1,1,1,3,3,3-hexafluoro-2-propanol to afford 5-trifluoromethyl-2-cyclopentenones. Both acyclic and cyclic substrates furnish the corresponding cyclized products in good to excellent yields with defined placement of the endocyclic double bond due to the strong electronic effect exerted by the trifluoromethyl group.

DOI： 10.1055/s-1998-1817

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Fluorine-Directed Nazarov Cyclizations 2 : Regioselective Synthesis of 5-Trifluoromethyl-2-2cyclopentenones 査読有り

岡内　辰夫

Synlett ( 8 ) 927 - 929 1998年04月

Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents 査読有り

岡内　辰夫

The Journal of Organic Chemistry 63 ( 18 ) 6239 - 6246 1998年04月

Lewis Acid-Catalyzed Intramodecular [2+2]Cydoaddition of α-Ester-Substituted Conjugated Dienyl and Trienylphosphonates. New Synthesis of Functionalized Cydic Terpenoids 査読有り

岡内　辰夫

The Journal of Organic Chemistry 62 ( 24 ) 8419 - 8424 1997年04月

2-Phosphono-1,1,4,4-tetrathio-1,3-butadienes. Synthesis and Synthetic Application to Highly Functionalized Dienes and Heterocycles 査読有り

岡内　辰夫

Bulletin des Soci(]J1117[)t(]J1117[)s Chimique Belges 106 ( 9-10 ) 525 - 532 1997年04月

5-endo-Trigonal Cyclization of o-Substituted gem-Difluorostyrenes : Syntheses of 2-Fluorinated Indoles, Benzo[b]furans, and Benzo[b]thiophenes 査読有り

岡内　辰夫

Chemical Communications ( 16 ) 1537 - 1538 1997年04月

5-endo-Trigonal cyclization of o-substituted gem-difluorostyrenes: Syntheses of 2-fluorinated indoles, benzo[b]furans and benzo[b]thiophenes 査読有り

Ichikawa J., Wada Y., Okauchi T., Minami T.

Chemical Communications ( 16 ) 1537 - 1538 1997年01月

記述言語：英語掲載種別：研究論文（学術雑誌）

β,β-Difluorostyrenes bearing tosylamido, hydroxy or methylsulfinyl groups at the o-position undergo intramolecular substitution of the nitrogen, oxygen or sulfur with loss of fluorine via a 5-endo-trigonal process leading to 2-fluorinated heterocyclic systems in high yields.

DOI： 10.1039/a703110f

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Lewis Acid-Catalyzed Intramolecular [2 + 2] Cycloaddition of α-Ester-Substituted Conjugated Dienyl- And Trienylphosphonates. New Synthesis of Functionalized Cyclic Terpenoids 査読有り

Okauchi T., Kakiuchi T., Kitamura N., Utsunomiya T., Ichikawa J., Minami T.

Journal of Organic Chemistry 62 ( 24 ) 8419 - 8424 1997年01月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

α-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by the Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddition in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yield) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar treatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosphonate 12 resulted in the formation of ionone derivatives (30-94% yield). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an ester group.

DOI： 10.1021/jo971153g

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Synthesis and synthetic application of phosphonoketene dithioacetals. New synthesis of dithioallenes and (α-dithiocarboxyvinyl)phosphonates 査読有り

Minami T., Okauchi T., Matsuki H., Nakamura M., Ichikawa J., Ishida M.

Journal of Organic Chemistry 61 ( 23 ) 8132 - 8140 1996年11月

記述言語：英語掲載種別：研究論文（学術雑誌）

Phosphonoketene dithioacetals 3a-e were obtained in good yields by the reaction of ethyl phosphonoacetates 1a,b with 2-4 equiv of thiols 2a-c in the presence of an alkylaluminum dichloride or dialkylaluminum chlorides. Reaction of 2,2-dithio-1-phosphonovinyl anions with aldehydes afforded allylic alcohols 4-7, 11-18 in good to moderate yields. Treatment of the alcohols 4-6 with t-BuOK in THF led to symmetrical [2 + 2] cycloadducts 20-22 of 1,1-(ethylenedithio)allenes in moderate yields, while a similar reaction of the alcohols 11-13 produced a mixture of symmetrical and unsymmetrical [2 + 2] cycloadducts of 1,1-(trimethylenedithio)allenes, 23a-25a and 23b-25b, in 55-94% yields. The alcohol 15 on a similar treatment gave 3-tert-butyl-1,1-bis(ethylthio)allene (26) in quantitative yield. The structures of 20 and 23b were determined by X-ray analysis. Treatment of the alcohols 15 and 18 with trifluoromethanesulfonic acid/n-Bu4NX (X = Br, I) or triphenylphosphine/CBr4 in CH2Cl2 afforded α-phosphonodithioacryclic acid esters 34 and 35 in 25-52% yields. The tandem Michael-Wittig reaction of 35 with sodium salt of 2-pyrrolecarbaldehyde in DMF gave ethyl 3-phenyl-3H-cyclopenta[a]pyrrole-2-dithiocarboxylate (36) in 25% yield.

DOI： 10.1021/jo960491z

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Development of Chiral Phosphine Ligands Bearing a Carboxyl Group and Their Application to Catalytic Asymmetric Reaction 査読有り

岡内　辰夫

Tetrahedron : Asymmetry 6 ( 10 ) 2469 - 2474 1996年04月

synthesis and Synthetic Application of Phosphonoketene Dithioacetals. New Synthesis of Dithioallenes and (α-Dithio carboxyvinyl) phosphonatis. 査読有り

岡内　辰夫

The Journal of Organic Chemistry 23 ( 61 ) 8132 - 8140 1996年04月

Novel 2, 2-Difluorovinylzirconocene : A Facile Synthesis of Monosubstituted gem-Difluoroolefins via Its Cross-Coupling Reaction 査読有り

岡内　辰夫

Tetrahedron Letters 37 ( 48 ) 8799 - 8802 1996年04月

Development of chiral phosphine ligands bearing a carboxyl group and their application to catalytic asymmetric reaction 査読有り

Minami T., Okada Y., Otaguro T., Tawaraya S., Furuichi T., Okauchi T.

Tetrahedron: Asymmetry 6 ( 10 ) 2469 - 2474 1995年10月

記述言語：英語掲載種別：研究論文（学術雑誌）

A new chiral phosphine ligand bearing a carboxyl group, 3-(diphenylphosphino)butanoic acid, was developed and used for palladium catalyzed asymmetric allylic alkylation of cyclic cis-allylic acetates such as 2-cyclopentenyl, 2-cyclohexenyl, and 2-cycloheptenyl acetate. These acetates reacted with triethyl sodiophosphonoacetate in the presence of the palladium catalyst with the ligand to give the corresponding alkylation products in good enantiomeric excesses. © 1995.

DOI： 10.1016/0957-4166(95)00322-G

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Novel 6-5 Fused Ring Heterocycle Antifolates with Potent Antitumor Activity : Bridge Modifications and Heterocyclic Benzoyl Isosters of 2, 4-Diamino-6, 7-dihydro-5H-cyclopenta[d]pyrimidine Antifolate 査読有り

岡内　辰夫

Chemical & Pharmaceutical Bulletin 43 ( 5 ) 829 - 841 1995年04月

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