研究成果 Publication

2024

  • Iridium/chiral phosphoramidite-olefine complex catalysed enantioselective [3+2] annulation of ortho-ketoarylboron compounds with conjugated dienes

Ryota Yabe, Takahiro Nishimura*

Chem. Commun. 2024, 60, 13211–13214.

DOI:10.39/D4CC04238G

cc2024-1

  • Synthesis of Tricyclic Fused 6−5−4 Carbocycles via Acid-Promoted Cascade Intramolecular Cyclization of Allenylsilane-Tethered Cyclohexadienones

Yuka Iwakiri, Ryoma Kishimoto, Kazuhiko Sakaguchi,* Takahiro Nishimura

Org. Lett. 2024, 26, 3475–3480.

DOI:10.1021/acs.orglett.4c01108

ol2024

2023

  • Iridium-catalyzed asymmetric addition of imides to alkenes

Kentaro Yamakawa, Kana Sakamoto, Takahiro Nishimura*

Chem. Commun. 2023, 59, 12871–12874.

DOI: 10.1039/d3cc04406h

cc2023-2

  • Iridium-Catalyzed Branch-Selective and Enantioselective C2-Alkylation of N-Benzimidazolyl Indoles

Kentaro Yamakawa, Takahiro Nishimura*

Adv. Synth. Catal. 2023, 365, 2013–2017.

DOI:10.1002/adsc.202300370

asc2023-2

  • Ruthenium-catalysed N-alkylation of anilines with primary carbohydrate alcohols via borrowing hydrogen strategy

Kouki Tsuge, Shunnichi Kubota, Kana Sakamoto, Kenji Kitayama, Takahiro Nishimura*

Chem. Commun. 2023, 59, 7052–7055.

DOI:10.1039/D3CC01931D

cc2023

  • Synthesis of Chiral Spiro[4.5]decadienones via Chirality-transferring Oxidative Intramolecular Cyclization of Allenylsilane-tethered Phenols

Ryoma Kishimoto, Yuka Iwakiri, Kazuhiko Sakaguchi,* Takahiro Nishimura

Synthesis 2023, 55, 2713–2729.

DOI:10.1055/a-2075-3258

synthesis2023

  • Ir-Catalyzed α-Alkylation of Methyl Ketones with Primary Carbohydrate Alcohols

Kouki Tsuge, Shunnichi Kubota, Kana Sakamoto, Kenji Kitayama, Takahiro Nishimura*

Adv. Synth. Catal. 2023, 365, 971–975.

DOI:10.1002/adsc.202300124

asc2023

  • Iridium-Catalyzed Enantioselective Intermolecular Hydroarylation of 1,1-Disubstituted Alkenes

Kentaro Yamakawa, Ikumi Nakamura, Kana Sakamoto, Takahiro Nishimura*

J. Org. Chem. 2023, 88, 7858–7862.

DOI:10.1021/acs.joc.2c02619

joc2023

2022

  • Asymmetric addition of an N-methyl C(sp3)–H bond to cyclic alkenes enabled by an iridium/phosphine-olefin catalyst

Kana Sakamoto and Takahiro Nishimura*

Chem. Commun. 2022, 58, 11783-11786. Selected as the outside front cover.

DOI:10.1039/D2CC04642C.

Featured in Synfacts 2022, 18, 1319.

cc2022-2

  • Iridium-Catalyzed Enantioselective Direct α-C–H Alkylation of Saturated Cyclic Amines with Alkenes

Daisuke Yamauchi, Kentaro Yamakawa, and Takahiro Nishimura*

Org. Lett. 2022, 24, 6828–6833.

DOI:10.1021/acs.orglett.2c02733.

Featured in Org. Chem. Highlights.

ol2022

  • Ir-catalyzed cyclization of α,ω-dienes with an N-methyl group via two C–H activation steps

Katsumasa Tanaka, Hiroshi Hattori, Ryota Yabe, and Takahiro Nishimura*

Chem. Commun. 2022, 58, 5371–5374.

DOI:10.1039/D2CC01275H.

cc2022

  • Enantioselective C–H Alkylation of N-Arylbenzamides with Vinyl Ethers Catalyzed by an Iridium/Chiral Phosphoramidite–Olefin Complex

Kotone Murakami, Kana Sakamoto, and Takahiro Nishimura*

Synthesis 2022, 54, 4753-4763.

DOI:10.1055/a-1672-6284.

s2021-2

2021

  • Iridium-catalyzed enantioselective addition of an N-methyl C–H bond to α-trifluoromethylstyrenes via C–H activation

Daisuke Yamauchi, Ikumi Nakamura, and Takahiro Nishimura*

Chem. Commun. 2021, 57, 11787–11790. Selected as the inside front cover.

DOI: 10.1039/D1CC05076A.

cc2021-2

  • Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β‑Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones

Shoma Ariyoshi, Kazuhiko Sakaguchi,* and Takahiro Nishimura

J. Org. Chem. 2021, 86, 11884-11894.

DOI: 10.1021/acs.joc.1c01284

JOC2021

  • Iridium-catalyzed stereoselective [3+2] annulation of α-oxocarboxylic acids with 1,3-dienes

Ryota Yabe, Yusuke Ebe, and Takahiro Nishimura*

Chem. Commun. 2021, 57, 5917-5920.

DOI: 10.1039/D1CC02003J.

cc2021

  • Iridium-Catalyzed Direct C–H Allylation of Ketimines

Ryota Yabe, Yusuke Ebe, and Takahiro Nishimura*

Synthesis 2021, 53, 3051-3056.

DOI: 10.1055/a-1477-7059.

s2021

  • Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation

Kana Sakamoto and Takahiro Nishimura*

Org. Biomol. Chem. 2021, 19, 684–690.

DOI: 10.1039/D0OB02421J

obc2021

    • Iridium-Catalyzed Hydroarylation via C–H Bond Activation

    Takahiro Nishimura

    Chem. Rec., 2021, 21, 3532–3545.

    DOI: 10.1002/tcr.202100109.

    2020

    • Enantioselective Synthesis of Chiral Indane Derivatives by Rhodium-Catalyzed Addition of Arylboron Reagents to Substituted Indenes

    Moeko Umeda, Hikaru Noguchi, and Takahiro Nishimura*

    Org. Lett. 2020, 22, 9597–9602.

    DOI: 10.1021/acs.orglett.0c03651

    ol2020

    • Synthesis of Allene-containing Apocarotenoids by Cross-coupling Strategy

    Kazuhiko Sakaguchi,* Yuto Nishioka, Naoto Kinashi, Nao Yukihira, Tetsuro Shinada, Takahiro Nishimura, Hideki Hashimoto, and Shigeo Katsumura

    Synthesis 2020, 52, 3007–3017.

    DOI: 10.1055/s-0040-1707906

    synthesis2020

    • Iridium-catalyzed Annulation of α,β-Unsaturated Amides with Electron-deficient Conjugated Dienes

    Kotone Murakami, Midori Nagamoto, and Takahiro Nishimura*

    Chem. Lett. 2020, 49, 732–735.

    DOI:10.1246/cl.200193

    cl2020

    2019

    • Rhodium-catalyzed asymmetric addition of arylboronic acids to 2H-chromenes leading to 3-arylchromane derivatives

    Moeko Umeda, Kana Sakamoto, Tomotaka Nagai, Midori Nagamoto, Yusuke Ebe, and Takahiro Nishimura*

    Chem. Commun. 2019, 55, 11876–11879.

    DOI:10.1039/C9CC06221A

    cc2019

    • Acid-Catalyzed Chirality-Transferring Intramolecular Friedel–Crafts Cyclization of α-Hydroxy-α-alkenylsilanes

    Kazuhiko Sakaguchi,* Shunnichi Kubota, Wataru Akagi, Naoko Ikeda, Masato Higashino, Shoma Ariyoshi, Tetsuro Shinada, Yasufumi Ohfune and Takahiro Nishimura

    Chem. Commun. 2019, 55, 8635–8638.

    DOI:10.1039/c9cc03509e

    chemcommun2019

    • Iridium-Catalyzed Asymmetric Hydroarylation of Chromene Derivatives with Aromatic Ketones: Enantioselective Synthesis of 2-Arylchromanes

    Kana Sakamoto and Takahiro Nishimura*

    Adv. Synth. Catal. 2019, 361, 2124–2128. Selected as a "VIP" with Inside Cover Picture.

    DOI:10.1002/adsc.201801664

    adsc2019

    • Iridium-Catalyzed Direct Hydroarylation of Glycals via C–H Activation: Ligand-Controlled Stereoselective Synthesis of α- and β-C-Glycosyl Arenes

    Kana Sakamoto, Masaki Nagai, Yusuke Ebe, Hideki Yorimitsu, and Takahiro Nishimura*

    ACS Catal. 2019, 9, 1347–1352.

    DOI:10.1021/acscatal.8b04686

    Featured in Synfacts 2019, 15, 0599.

    acscat2019

    2018

    • Iridium-Catalyzed Sequential sp3 C–H Alkylation of an N-Methyl Group with Alkenes Towards the Synthesis of α-Substituted Amines

    Hiroshi Hattori and Takahiro Nishimura*

    Adv. Synth. Catal. 2018, 360, 4827–4831.

    DOI:10.1002/adsc.201801131
    Featured in Org. Chem. Highlights.

    asc2018

    • Hydroxoiridium-Catalyzed sp3 C−H Alkylation of Indoline Derivatives with Terminal Alkenes

    Ikumi Nakamura, Daisuke Yamauchi, and Takahiro Nishimura*

    Asian J. Org. Chem. 2018, 7, 1347–1350.

    DOI:10.1002/ajoc.201800189

    ajoc2018

    • Stereocontrolled Synthesis of 19’-Deoxyperidinin

    Naoto Kinashi, Shigeo Katsumura,* Tetsuro Shinada, and Kazuhiko Sakaguchi*

    Org. Lett. 2018, 20, 582–585.

    DOI:10.1021/acs.orglett.7b03695

    ol2018-2

    • Iridium-Catalyzed Hydroarylation of Conjugated Dienes via π-Allyliridium Intermediates

    Midori Nagamoto, Hideki Yorimitsu, and Takahiro Nishimura*

    Org. Lett. 2018, 20, 828–831.

    DOI:10.1021/acs.orglett.7b03969

    ol2018

    • Iridium/Chiral Diene-Catalyzed Enantioselective (3 + 2) Annulation of Aromatic Ketimines with 1,3-Enynes

    Midori Nagamoto, Kana Sakamoto, and Takahiro Nishimura*

    Adv. Synth. Catal. 2018, 360, 791–795.

    DOI:10.1002/adsc.201701378

    asc2017

    2017

    • Stereocontrolled Synthesis of Paracentrone

    Yuto Nishioka, Yo Yano, Naoto Kinashi, Natsumi Oku, Youhei Toriyama, Shigeo Katsumura,* Tetsuro Shinada, Kazuhiko Sakaguchi*

    Synlett 2017, 28, 327-332.

    DOI: 10.1055/s-0036-1588906

    Synlett2017

    • Hydroxoiridium-Catalyzed Hydroarylation of Alkynes and Bicycloalkenes with N-Sulfonylbenzamides

    Midori Nagamoto, Jun-ichi Fukuda, Miyuki Hatano, Hideki Yorimitsu, and Takahiro Nishimura*

    Org. Lett. 2017, 19, 5952−5955.

    DOI: 10.1021/acs.orglett.7b02950

    ol2017

    • Iridium-Catalyzed Intramolecular Oxidative Cyclization of Alkenyl Amides and Alkenoic Acids

    Midori Nagamoto, Takahiro Nishimura,* and Hideki Yorimitsu

    Synthesis 2017, 49, 4272–4282.

    DOI: 10.1055/s-0036-1588435

    2

    • Iridium-catalyzed sp3 C–H Alkylation of 3-Carbonyl-2-(alkylamino)pyridines with Alkenes

    Masaki Nagai, Midori Nagamoto, Takahiro Nishimura,* and Hideki Yorimitsu

    Chem. Lett. 2017, 46, 1176–1178.

    DOI: 10.1246/cl.170373

    3

    • Iridium-catalyzed Cleavage of C–O Bonds Using Alcohols as Reducing Reagents

    Yuta Hibe, Yusuke Ebe, Takahiro Nishimura,* and Hideki Yorimitsu

    Chem. Lett. 2017, 46, 953–955.

    DOI: 10.1246/cl.170239

    4

    • Hydroxoiridium-Catalyzed Hydroalkylation of Terminal Alkenes with Ureas by C(sp3)–H Bond Activation

    Daisuke Yamauchi, Takahiro Nishimura,* and Hideki Yorimitsu

    Angew. Chem., Int. Ed. 2017, 56, 7200–7204.

    DOI: 10.1002/anie.201702169

    5

    • Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization

    Yusuke Ebe, Mitsuki Onoda, Takahiro Nishimura,* and Hideki Yorimitsu

    Angew. Chem., Int. Ed. 2017, 56, 5607–5611.

    DOI: 10.1002/anie.201702286

    6

    • Asymmetric hydroarylation of vinyl ethers catalyzed by a hydroxoiridium complex: azoles as effective directing groups

    Daisuke Yamauchi, Takahiro Nishimura,* and Hideki Yorimitsu

    Chem. Commun. 2017, 53, 2760–2763.

    DOI: 10.1039/c7cc00238f

    7

    • Regularized Regression Analysis of Digitized Molecular Structures in Organic Reactions for Quantification of Steric Effects

    Shigeru Yamaguchi,* Takahiro Nishimura, Yuta Hibe, Masaki Nagai, Hirofumi Sato, and Ian Johnston

    J. Comput. Chem. 2017, 38, 1825–1833.

    DOI: 10.1002/jcc.24791

    2016

    • Preparation of E-α-Stannyl-β-trimethylsilylethynylacrylate, Building Block for Polyconjugated Ylidenebutenolide and Its Derivatives, by Novel E-Selective Ethynylstannylation of Propiolate

    Naoto Kinashi, Kazuhiko Sakaguchi,* Shigeo Katsumura,* Tetsuro Shinada

    Tetrahedron Lett. 2016, 57, 129-132.

    DOI: 10.1016/j.tetlet.2015.11.079

    TL2016

    • Asymmetric Cyclization of N-Sulfonyl Alkenyl Amides Catalyzed by Iridium/Chiral Diene Complexes

    Midori Nagamoto, Tomoyuki Yanagi,Takahiro Nishimura,* and Hideki Yorimitsu

    Org. Lett. 2016, 18, 4474−4477.

    DOI: 10.1021/acs.orglett.6b01954

    8

    • Selective H/D Exchange at Vinyl and Methylidene Groups with D2O Catalyzed by an Iridium Complex

    Miyuki Hatano, Takahiro Nishimura,* and Hideki Yorimitsu

    Org. Lett. 2016, 18, 3674−3677.

    DOI: 10.1021/acs.orglett.6b01721

    9

    • Iridium-catalyzed asymmetric [3+2] annulation of aromatic ketimines with alkynes via C–H activation: unexpected inversion of the enantioselectivity induced by protic acids

    Midori Nagamoto, Daisuke Yamauchi, and Takahiro Nishimura*

    Chem. Commun. 2016, 52, 5876–5879.

    DOI: 10.1039/c6cc01398h

    Highlighted in Synfacts, Synfacts 2016, 12, 597.

    10

    • Asymmetric Alkylation of N-Sulfonylbenzamides with Vinyl Ethers via C−H Bond Activation Catalyzed by Hydroxoiridium/Chiral Diene Complexes

    Miyuki Hatano, Yusuke Ebe, Takahiro Nishimura,* and Hideki Yorimitsu

    J. Am. Chem. Soc. 2016, 138, 4010−4013.

    DOI: 10.1021/jacs.6b01591

    Highlighted in Synfacts, Synfacts 2016, 12, 596.

    11

    • Rhodium-Catalyzed Enantioselective Addition of Tricyclopropylboroxin to N-Sulfonylimines

    Takahiro Nishimura,* Tomotaka Nagai, Ryosuke Takechi, Yusuke Ebe

    Synthesis 2016, 48, 2612–2618.

    DOI: 10.1055/s-0035-1561605

    Highlighted in Synfacts, Synfacts 2016, 12, 699.

    12

    2015

    • Stereoselective hydroacylation of bicyclic alkenes with 2-hydroxybenzaldehydes catalyzed by hydroxoiridium/diene complexes

    Midori Nagamoto and Takahiro Nishimura*

    Chem. Commun. 2015, 51, 13791–13794.

    DOI: 10.1039/C5CC05432J

    Highlighted in Synfacts, Synfacts 2015, 11, 1064.

    13

    • Iridium-catalyzed asymmetric cyclization of alkenoic acids leading to γ-lactones

    Midori Nagamoto and Takahiro Nishimura*

    Chem. Commun. 2015, 51, 13466–13469.

    DOI: 10.1039/C5CC05393E

    Highlighted in Synfacts, Synfacts 2016, 12, 64.

    14

    • Hydroxoiridium/Chiral Diene Complexes as Effective Catalysts for Asymmetric Annulation of α-Oxo- and Imino-carboxamides with 1,3-Dienes

    Miyuki Hatano and Takahiro Nishimura*

    Angew. Chem., Int. Ed. 2015, 54, 10949–10952.

    DOI: 10.1002/anie.201505382

    15

    • Formation of Carbocycles via a 1,4-Rh Shift Triggered by a Rhodium-Catalyzed Addition of Terminal Alkynes to 3,3-Diarylcyclopropenes

    Takahiro Sawano, Minoru Hashizume, Shouta Nishimoto, Keiyu Ou, and Takahiro Nishimura*

    Org. Lett. 2015, 17, 2630–2633.

    DOI: 10.1021/acs.orglett.5b00984

    16

    • Iridium-Catalyzed Branch-Selective Hydroarylation of Vinyl Ethers via C–H Bond Activation

    Yusuke Ebe and Takahiro Nishimura*

    J. Am. Chem. Soc. 2015, 137, 5899−5902.

    DOI: 10.1021/jacs.5b03099

    Highlighted in Synfacts, Synfacts 2015, 11, 723.

    17

    • Enantioselective 1,4-addition of cyclopropylboronic acid catalyzed by rhodium/chiral diene complexes

    Ryosuke Takechi and Takahiro Nishimura*

    Chem. Commun. 2015, 51, 8528–8531.

    DOI: 10.1039/c5cc02140e

    Highlighted in Synfacts, Synfacts 2015, 11, 747.

    18

    • Rhodium-catalyzed asymmetric addition of arylboronic acids to cyclic N-sulfonyl ketimines towards the synthesis of α,α-diaryl-α-amino acid derivatives

    Ryosuke Takechi and Takahiro Nishimura*

    Org. Biomol. Chem. 2015, 13, 4918–4924.

    DOI: 10.1039/c5ob00431d

    19

    • Iridium-Catalyzed Annulation of Aromatic Imines with 1,3-Dienes via Direct Functionalization of an Aromatic C–H Bond

    Yusuke Ebe, Miyuki Hatano, and Takahiro Nishimura*

    Adv. Synth. Catal. 2015, 357, 1425–1436. (VIP)

    DOI: 10.1002/adsc.201401171

    20

    2014

    • Straightforward synthesis of fucoxanthin short-chain derivatives via modified-Julia olefination

    Satoshi Okumura, Takayuki Kajikawa, Koki Yano, Kazuhiko Sakaguchi, Daisuke Kosumi, Hideki Hashimoto, Shigeo

    Katsumura*

    Tetrahedron Lett. 2014, 55,, 407-410.

    DOI: 10.1016/j.tetlet.2013.11.043

    TL2014

    • Iridium-Catalyzed Annulation of Salicylimines with 1,3-Dienes

    Yusuke Ebe and Takahiro Nishimura*

    J. Am. Chem. Soc. 2014, 136, 9284–9287.

    DOI: 10.1021/ja504990a

    Highlighted in Synfacts as Synfact of the month, Synfacts 2014, 10, 931.

    21

    • Catalytic [3 + 2] annulation of ketimines with alkynes via C–H activation by a cationic iridium(cod) complex

    Midori Nagamoto and Takahiro Nishimura*

    Chem. Commun. 2014, 50, 6274–6277.

    DOI: 10.1039/C4CC01874E

    22

    2013

    • Enantioselective [3 + 2] annulation via C–H activation between cyclic N-acyl ketimines and 1,3-dienes catalyzed by iridium/chiral diene complexes

    Takahiro Nishimura,* Midori Nagamoto, Yusuke Ebe, and Tamio Hayashi

    Chem. Sci. 2013, 4, 4499–4504.

    DOI: 10.1039/c3sc52379a

    Highlighted in Synfacts as Synfact of the month, Synfacts 2014, 10, 157.

    23

    • Cobalt-Catalyzed Asymmetric Addition of Silylacetylenes to 1,1-Disubstituted Allenes

    Takahiro Sawano, Keiyu Ou, Takahiro Nishimura,* and Tamio Hayashi

    J. Org. Chem. 2013, 78, 8986−8993. [Featured Article]

    DOI: 10.1021/jo401604n

    Highlighted in Synfacts, Synfacts 2013, 8, 1321.

    24

    • Asymmetric Synthesis of gem-Diaryl Substituted Cyclic Sulfamidates and Sufamides by Rhodium-Catalyzed Arylation of Cyclic Ketimines

    Takahiro Nishimura,* Yusuke Ebe, Hiroto Fujimoto, and Tamio Hayashi

    Chem. Commun. 2013, 49, 5504–5506.

    DOI: 10.1039/C3CC42071J

    25

    • Rhodium-Catalyzed Asymmetric Cycloisomerization of 1,6-Ene-ynamides

    Takahiro Nishimura,* Yuka Takiguchi, Yuko Maeda, and Tamio Hayashi*

    Adv. Synth. Catal. 2013, 355, 1374–1382.

    DOI: 10.1002/adsc.201300148

    26

    • Iridium-Catalyzed [3+2] Annulation of Cyclic N-Sulfonyl Ketimines with 1,3-Dienes via C-H Activation

    Takahiro Nishimura,* Yusuke Ebe, and Tamio Hayashi

    J. Am. Chem. Soc. 2013, 135, 2092–2095.

    DOI: 10.1021/ja311968d

    Highlighted in Synfacts as Synfact of the month, Synfacts 2013, 9, 503.

    27

    • Hydroxorhodium/Chiral Diene Complexes as Effective Catalysts for the Asymmetric Arylation of 3-Aryl-3-hydroxyisoindolin-1-ones

    Takahiro Nishimura,* Akira Noishiki, Yusuke Ebe, and Tamio Hayashi*

    Angew. Chem., Int. Ed. 2013, 52, 1777–1780.

    DOI: 10.1002/anie201208593

    Highlighted in Synfacts, Synfacts 2013, 9, 401.

    28

    2012年以前は、コチラ（cv,publication list）をご参照ください。