論文 - 有光　暁

Importance of C-H Hydrogen Bonding in Asymmetric Catalysis

Arimitsu, S; Higashi, M

NONCOVALENT INTERACTIONS IN CATALYSIS   36   26 - 65   2019年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

Diastereoselective synthesis of 5,5-disubstituted 3,3-difluorotetrahydrofurans

Satoru Arimitsu, Makoto Nakasone, Emi Gima

Tetrahedron Letters ( Elsevier Ltd )  59 ( 10 ) 887 - 890   2018年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2018 Elsevier Ltd The diastereoselective synthesis of 5,5-disubstituted 3,3-difluorotetrahydrofurans 2 was achieved using β,β-difluorohomoallylic alcohols 1 as the key starting material in the presence of ICl (3.0 equiv) and tert-BuOK (1.5 equiv) in THF. The corresponding iodocyclization products 2 were obtained in good to moderate yields with excellent diastereo- and regioselectivities (d.r. = >20/1, 5-endo-trig only).

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Stereoselective Synthesis of 4-Substituted 2,4-Dichloro-2-butenals by α- And γ-Regioselective Double Chlorination of Dienamine Catalysis

Satoru Arimitsu, Kazuto Terukina, Tatsuro Ishikawa

Synlett ( Synlett )  29 ( 14 ) 1887 - 1891   2018年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© Georg Thieme Verlag Stuttgart New York. The L-proline-catalyzed reaction of enolizable α,β-unsaturated aldehydes with N-chlorosuccinimide (NCS) gave the corresponding 4-substituted 2,4-dichloro-2-butenals with moderate yields and excellent diastereoselectivities (Z / E = >20/1) through consecutive double chlorination at the α- and γ-positions of the dienamine intermediate. The corresponding 2,4-dichloro-2-butenals contain a multireactive 1,3-dichloro allylic unit useful for the construction of Z -vinyl chlorides; the chloride on the allylic position was replaced with mild nucleophiles such as MeOH and EtOH via an S N 2 substitution reaction, and its aldehyde moiety was used as a synthetic handle and transformed into an alcohol or a vinyl group. All products obtained after those synthetic manipulations maintained excellent diastereoselectivities (Z/E = >20/1).

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Cinchona-Based Primary Amine Catalyzed a Proximal Functionalization of Dienamines: Asymmetric α-Fluorination of α-Branched Enals

Satoru Arimitsu, Tsunaki Yonamine, Masahiro Higashi

ACS Catalysis ( AMER CHEMICAL SOC )  7 ( 7 ) 4736 - 4740   2017年07月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2017 American Chemical Society. Fluorination of dienamines generated by α-branched enals and 6′-hydroxy-9-amino-9-deoxy-epi-quinidine (30 mol %) with NSFI show excellent α-regioselectivity to construct allylic fluorides containing a highly stereocontrolled quaternary fluorinated carbon (E/Z ≥ 20/1 and up to 93% enantiometric excess (ee)). By DFT calculation, the quinuclidine moiety of the catalyst was shown to function as a coordinating group to promote a reaction at the proximal α-position, and the nonclassical CH hydrogen bond plays an important role in the high enantioselectivity.

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A new umpolung for direct γ-regioselective nucleophilic addition of alcohols to γ-enolizable α,β-unsaturated aldehydes

Satoru Arimitsu, Mari Oshiro, Tsunaki Yonamine

Tetrahedron Letters ( PERGAMON-ELSEVIER SCIENCE LTD )  58 ( 25 ) 2517 - 2520   2017年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2017 Elsevier Ltd A direct γ-regioselective nucleophilic addition of alcohols toward γ-enolizable α,β-unsaturated aldehydes was developed using a catalytic amount of MeSO3H (30 mol%) and a stoichiometric amount of chloranil (1.0 equiv) as the oxidant. The addition of hexafluoroisopropanol (HFIP) was found to accelerate this cross-dehydrogenative coupling, furnishing diverse alcoholic adducts with high γ-regio- and E-stereoselectivities.

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Stereoselective Organocatalytic Synthesis of α,α-Difluoro-γ,γ-Disubstituted Butenals.

Arimitsu S, Nakasone M

The Journal of organic chemistry ( AMER CHEMICAL SOC )  81 ( 15 ) 6707 - 13   2016年08月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 American Chemical Society. A highly stereoselective reaction of α,α-difluoro-γ,γ-disubstituted butenals 2 bearing two different substituents at the γ position has been developed with an organocatalytic system of l-proline (30 mol %) and salicylic acid (60 mol %). This novel reaction demonstrated a wide substrate scope and excellent E stereoselectivity in most cases. The obtained difluorinated aldehyde 2a was applied as a useful synthetic precursor for constructing 3,3-disubstituted allylic difluoride moieties.

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Highly Stereoselective Synthesis of Fluoroalkene Dipeptides via the Novel Chromium(II)-Mediated Carbon-Fluorine Bond Cleavage/New Carbon-Carbon Bond Formation

Takashi Nihei, Yuji Nishi, Natsumi Ikeda, Saya Yokotani, Takashi Ishihara, Satoru Arimitsu, Tsutomu Konno

Synthesis (Germany) ( GEORG THIEME VERLAG KG )  48 ( 6 ) 865 - 881   2016年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 Georg Thieme Verlag Stuttgart. New York. An efficient chromium(II)-mediated reductive coupling reaction of various CBrF2-containing molecules and aldehydes has been developed. This reaction proceeds presumably via the monofluorinated dichromium(III) intermediate generated by the carbon-fluorine bond activation, and provides a general and straightforward access to synthesize a variety of (E)- or (Z)-β-fluoroallylic alcohols in a highly stereoselective manner. Based on the novel reductive coupling, four types of fluoroalkene dipeptide analogues could be stereoselectively prepared.

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One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides

Yoshiki Toma, Masataka Kunigami, K. jiro Watanabe, Masahiro Higashi, Satoru Arimitsu

Journal of Fluorine Chemistry ( ELSEVIER SCIENCE SA )  189   22 - 32   2016年 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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© 2016 Elsevier B.V. The reaction with β-trifluoromethyl acrylamide 3e and azomethine ylides generated from L-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities.

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Application of Tertiary Amines Synthesized by Catalytic Dehydrogenation of Enamines as Nucleophilic C₂ Synthons for 1,4-Conjugate Addition with Fluoroalkylated Olefins

Morigaki, A; Kawamura, M; Arimitsu, S; Ishihara, T; Konno, T

ASIAN JOURNAL OF ORGANIC CHEMISTRY   2 ( 3 ) 239 - 243   2013年03月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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Unusual annulation reaction of electron-deficient alkenes with enamines: an easy access to stereocontrolled 4-fluoroalkylated 3,4-dihydro-2<i>H</i>-pyrans

Morigaki, A; Tsukade, K; Arimitsu, S; Konno, T; Kubota, T

TETRAHEDRON   69 ( 5 ) 1521 - 1525   2013年02月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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The First Practical Additive-Free 1,4-Conjugated Alkylation of Fluoro-alkylated Electron-Deficient Olefins with Various Organozinc Reagents

Morigaki, A; Miyabe, T; Tsukade, K; Arimitsu, S; Ishihara, T; Konno, T

SYNTHESIS-STUTTGART   45 ( 1 ) 101 - 105   2013年01月 [ 査読有り ]

掲載種別: 研究論文（学術雑誌）

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An Achiral-Acid-Induced Switch in the Enantioselectivity of a Chiral cis-Diamine-Based Organocatalyst for Asymmetric Aldol and Mannich Reactions†

Dr. Shin A. Moteki, Jianwei Han, Satoru Arimitsu, Dr. Matsujiro Akakura, Keiji Nakayama and Prof. Dr. Keiji Maruoka1,*

ACIE ( その他の出版社 )  51 ( 5 ) 1187   2012年

掲載種別: 研究論文（その他学術会議資料等）

Design of Structurally Rigid trans-Diamine-Based Tf-Amide Organocatalysts with a Dihydroanthracene Framework for Asymmetric Conjugate Additions of Heterosubstituted Aldehydes to Vinyl Sulfones

Shin A. Moteki , Senmiao Xu , Satoru Arimitsu , and Keiji Maruoka *

JACS ( その他の出版社 )  132 ( 48 ) 17074   2010年

掲載種別: 研究論文（その他学術会議資料等）

Synthesis of 2, 4, 5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols

Satoru Arimitsu , Jesse M. Jacobsen , and Gerald B. Hammond *

JOC ( その他の出版社 )  73 ( 7 ) 2886   2008年

掲載種別: 研究論文（その他学術会議資料等）

Intramolecular Hydroamination of Difluoropropargyl Amides:  Regioselective Synthesis of Fluorinated β- and γ-Lactams

Santos Fustero, Begoña Fernández, Paula Bello, Carlos del Pozo, Satoru Arimitsu, and Gerald B. Hammond

OL ( その他の出版社 )  9 ( 21 ) 4251   2007年

掲載種別: 研究論文（その他学術会議資料等）