Asian Journal of Organic Chemistry

Cover image for Vol. 2 Issue 11

Special Issue: 40 Years of the Mukaiyama Aldol Reaction, 1973–2013

November 2013

Volume 2, Issue 11

Pages 885–996

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. You have free access to this content
      Cover Picture: (Asian J. Org. Chem. 11/2013) (page 885)

      Article first published online: 12 NOV 2013 | DOI: 10.1002/ajoc.201390030

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      The Mukaiyama aldol reaction is 40 years old this year. In this special issue we celebrate Professor Mukaiyama's seminal discovery and take a glimpse into the future by collecting together some of the latest research in directed aldol reactions. Even though the front cover looks like it might have arrived a month or so early, we think that all this top-quality research is more than just cause to celebrate at any time of the year! Photo credit: Jason Hollinger, http://flickr.com/photos/7147684@N03/543564833

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. You have free access to this content
  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
  5. Focus Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Nitroalkene Activation

      Secondary Amines as Lewis Bases in Nitroalkene Activation (pages 904–914)

      Dr. Wuming Yan, Prof. Dr. Xiaodong Shi and Dr. Cheng Zhong

      Article first published online: 1 AUG 2013 | DOI: 10.1002/ajoc.201300048

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      Second to none: Secondary amines are well-known enamine and iminium catalysts that can also be used as Lewis bases for the activation of electron-deficient olefins. In this Focus Review, a series of systematic studies on activation of nitroolefins with secondary amines as Lewis bases that give different multicomponent condensation products are described. Asymmetric syntheses of heterocycles based on this strategy are also presented.

  6. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Radical Cyclization

      Chiral Organotin Hydride Catalyzed Enantioselective Radical Cyclization of Aldehydes (pages 916–919)

      Dr. Seiji Shirakawa, Asuka Usui, Dr. S. B. Jennifer Kan and Prof. Dr. Keiji Maruoka

      Article first published online: 12 SEP 2013 | DOI: 10.1002/ajoc.201300138

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      Cat on a hot tin radical: Chiral organotin-hydride-catalyzed enantioselective radical cyclization of aldehydes has been achieved. The reaction is efficiently promoted by a catalytic amount (10 mol %) of a chiral tin hydride to produce chromanol derivatives with moderate enantioselectivity. The utility of chiral organotin hydride was also demonstrated in catalytic enantioselective radical reduction.

    2. Total Synthesis

      An Enantiodivergent Synthesis of (+)- and (−)-Centrolobines by Asymmetric Esterification Catalyzed by (R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) (pages 920–922)

      Dr. Kenya Nakata, Tatsuya Tokumaru, Prof. Dr. Hidetoshi Iwamoto, Prof. Dr. Yutaka Nishigaichi and Prof. Dr. Isamu Shiina

      Article first published online: 2 OCT 2013 | DOI: 10.1002/ajoc.201300139

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      Seventh heaven: The enantiodivergent synthesis of (+)- and (−)-centrolobines was achieved in a total of seven steps by using an asymmetric esterification in the presence of catalytic (R)-(+)-N-methylbenzoguanidine as the key reaction.

    3. [4+2] Cycloaddition

      Chemoselective Formal [4+2] Cycloaddition of 3-Hydroxycyclobutanones with Enones (pages 923–926)

      Kosuke Harada, Aya Nowaki and Prof. Dr. Jun-ichi Matsuo

      Article first published online: 2 OCT 2013 | DOI: 10.1002/ajoc.201300156

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      Choice cuts: The formal [4+2] cycloaddition of 3-hydroxycyclobutanones to α,β-unsaturated ketones proceeds chemoselectively at the α,β-carbon–carbon double bond to afford cyclohexanone derivatives by using boron trifluoride etherate as a Lewis acid. In contrast, 3-ethoxycyclobutanone reacts at the carbonyl carbon–oxygen double bond to give dihydro-γ-pyrones.

    4. Polyhydroxylated Compounds

      Specific Enhancement of Reactivity and Selectivity in the Substitution Reactions of Polyhydroxy Derivatives by Lithium Chloride (pages 927–930)

      Prof. Dr. Yutaka Watanabe, Mao Kawamoto, Hiroyuki Shintaku, Kae Tanabe, Dr. Hidetoshi Ohta and Dr. Minoru Hayashi

      Article first published online: 6 NOV 2013 | DOI: 10.1002/ajoc.201300163

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      Diol A for activation: LiCl mediates mono-O-substitution of vicinal diol derivatives that are capable of forming intramolecular hydrogen bonds. The remarkable selectivity that leads to mono-O-substitution was demonstrated in polyols such as cyclitols and saccharides. SM=starting material.

    5. Iodoaldol Reaction

      Diastereoselective Iodoaldol Reaction of γ-Alkoxy-α,β-Alkynyl Ketone Derivatives Promoted by Titanium Tetraiodide (pages 931–934)

      Dr. Iwao Hachiya, Shingo Ito, Shota Kayaki and Prof. Dr. Makoto Shimizu

      Article first published online: 22 OCT 2013 | DOI: 10.1002/ajoc.201300165

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      I, aldol: The iodoaldol reaction of γ-alkoxy-α,β-alkynyl ketones with aldehydes promoted by titanium tetraiodide proceeds to give the iodoaldol products in good yields with good to high diastereoselectivities. The iodinated addition products were transformed into tetrasubstituted furans by palladium-catalyzed Sonogashira coupling and subsequent cyclization. MOM=methoxymethyl ether.

    6. Electrochemical Chlorination

      Copper-Catalyzed Electrochemical Chlorination of 1,3-Dicarbonyl Compounds Using Hydrochloric Acid (pages 935–937)

      Kazuya Tsuchida, Dr. Takuya Kochi and Prof. Dr. Fumitoshi Kakiuchi

      Article first published online: 22 OCT 2013 | DOI: 10.1002/ajoc.201300168

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      Electric avenue: A copper-catalyzed electrochemical α-chlorination of 1,3-dicarbonyl compounds using hydrochloric acid as a chlorine source is described. Monochlorination products can be obtained from various 1,3-dicarbonyl compounds by using a reaction system where the only required reagents are a substrate, a solvent, a copper(II) salt and hydrochloric acid.

    7. C[BOND]H/C[BOND]N Arylation

      Palladium-Catalyzed C[BOND]H and C[BOND]N Arylation of Aminothiazoles with Arylboronic Acids (pages 938–942)

      Takahiro N. Uehara, Prof. Dr. Junichiro Yamaguchi and Prof. Dr. Kenichiro Itami

      Article first published online: 11 OCT 2013 | DOI: 10.1002/ajoc.201300172

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      A C4-selective C[BOND]H arylation of 2-aminothiazoles with arylboronic acids takes place under the influence of Pd(OAc)2/phen/TEMPO/LiBF4 in air. During this study, a Pd-catalyzed C[BOND]N cleavage/arylation of 2-aminobenzothiazoles with arylboronic acids has been discovered. bipy=2,2-bipyridyl; TEMPO=2,2,6,6-tetramethylpiperidin-1-oxyl.

    8. Transfer Hydrogenation

      Enantioselective Transfer Hydrogenation of Difluoromethyl Ketimines Using Benzothiazoline as a Hydrogen Donor in Combination with a Chiral Phosphoric Acid (pages 943–946)

      Dr. Tsubasa Sakamoto, Kosaku Horiguchi, Dr. Kodai Saito, Dr. Keiji Mori and Prof. Dr. Takahiko Akiyama

      Article first published online: 15 OCT 2013 | DOI: 10.1002/ajoc.201300174

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      Hold the benzothiazoline: Highly enantioselective transfer hydrogenation of difluoromethyl ketimines with benzothiazolines catalyzed by a chiral phosphoric acid furnishes α-difluoromethylated amines in good yields and with excellent enantioselectivity, irrespective of the stereochemistry of the starting materials. PMP=p-methoxyphenyl.

    9. Biomass Conversion

      Catalytic Conversion of Inert Carbohydrates into Platform Chemical 5-Hydroxymethylfurfural Using Arylboronic Acids (pages 947–951)

      Daniel H. Lukamto, Peng Wang and Prof. Dr. Teck-Peng Loh

      Article first published online: 5 NOV 2013 | DOI: 10.1002/ajoc.201300185

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      Looking forward: As fossil fuels deplete, 5-hydroxymethylfurfural (HMF) will play an important role in securing future energy and chemical feedstock needs as it is obtainable from renewable resources such as glucose and cellulose. We report a group of nonmetal Lewis-acid arylboronic acids that catalyse the formation of HMF in 3-ethyl-1-methyl-3 H-imidazol-1-ium chloride ([EMIM]Cl) from glucose and cellulose. EWG=electron-withdrawing group.

    10. Asymmetric Catalysis

      Chiral Supramolecular Magnesium(II) Binaphtholate Catalysts for the Enantioselective Direct Mannich-Type Reaction and Hetero-Diels–Alder Reaction (pages 952–956)

      Dr. Manabu Hatano, Dr. Takahiro Horibe, Kenji Yamashita and Prof. Dr. Kazuaki Ishihara

      Article first published online: 6 NOV 2013 | DOI: 10.1002/ajoc.201300190

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      Just another Mannich Mg: A recent development of chiral supramolecular magnesium(II) binaphtholates has inspired an investigation into two reactions, that is, the direct Mannich-type reaction and the hetero-Diels–Alder reaction, the mechanisms of which require further consideration. The results suggest that chiral di- and trinuclear supramolecular magnesium(II) complexes should play key roles as active catalytic species in these reactions. BINOL=1,1′-bi-2-naphthol.

    11. Mukaiyama Aldol Reaction

      Kinetics of the Chiral Disulfonimide-Catalyzed Mukaiyama Aldol Reaction (pages 957–960)

      Dr. Zhipeng Zhang and Prof. Dr. Benjamin List

      Article first published online: 4 NOV 2013 | DOI: 10.1002/ajoc.201300182

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      Making progress: The kinetics of the disulfonimide-catalyzed Mukaiyama aldol reaction have been established by using the reaction progress kinetic analysis (RPKA) method. The reaction is first order with respect to catalyst and silyl ketene acetal, and has an order of 0.55 with respect to the aldehyde, which suggests the reversibility of the binding between the aldehyde and the actual catalyst.

    12. Copper Catalysis

      Asymmetric Boron Conjugate Additions to Enones in Water Catalyzed by Copper(0) (pages 961–966)

      Taku Kitanosono and Prof. Dr. Shū Kobayashi

      Article first published online: 5 NOV 2013 | DOI: 10.1002/ajoc.201300201

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      Cop on to copper: An unprecedented copper(0) catalysis in water that entails chiral induction is proposed. A significant rate enhancement and stereocontrol are exerted discriminatorily in water. Several empirical facts suggest a new catalysis different from those of either copper(I) or copper(II) ions. The redox cycle mechanism proposed tentatively involves four steps (oxidative cyclometalation, transmetalation, hydrolysis, and reductive elimination).

  7. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Focus Review
    7. Communications
    8. Full Papers
    1. Alkyne Carboboration

      Nickel-Catalyzed Cyclizative trans-Carboboration of Alkynes through Activation of Boron–Chlorine Bonds by Using Organometallic Reagents as Donors of Organic Groups (pages 968–976)

      Dr. Masaki Daini, Dr. Akihiko Yamamoto and Prof. Dr. Michinori Suginome

      Article first published online: 10 OCT 2013 | DOI: 10.1002/ajoc.201300164

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      Triple take: Triggered by B[BOND]Cl bond activation, trans-addition of boron and carbon functional groups across a carbon–carbon triple bond takes place through transmetalation with alkynylstannanes and alkenylzirconium reagents, which leads to the synthesis of a variety of alkenylboronic acid derivatives.

    2. Aldol Polymerization

      Direct Aldol Polymerization of Acetaldehyde with Organocatalyst/Brønsted Acid Systems (pages 977–982)

      Shuhei Kusumoto, Dr. Shingo Ito and Prof. Dr. Kyoko Nozaki

      Article first published online: 17 SEP 2013 | DOI: 10.1002/ajoc.201300134

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      More haste, go direct: The direct aldol polymerization of acetaldehyde, a new approach for the synthesis of poly(vinyl alcohol) (PVA)- and poly(vinyl alcohol-co-ethylene) (EVA)-type oligomers, cooperatively catalyzed by organocatalysts and Brønsted acids was investigated. This conceptually new approach is an important step towards realizing the one-step synthesis of poly(vinyl alcohol)s from acetaldehyde with perfect atom economy.

    3. N-Acylphthalimide Chemistry

      Rhodium-Catalyzed Synthesis and Reactions of N-Acylphthalimides (pages 983–988)

      Dr. Guangzhe Li, Dr. Mieko Arisawa and Dr. Masahiko Yamaguchi

      Article first published online: 15 JUL 2013 | DOI: 10.1002/ajoc.201300094

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      Method of many talents: The synthesis and reactions of N-acylphthalimides are catalyzed by a complex of [RhH(PPh3)4] and 1,2-bis(diphenylphosphino)benzene (dppBz). N-Acylphthalimides can be synthesized by the imidation of thioesters or acid fluorides with N-(organothio)phthalimides. Thioesters, N-(phosphinoyl)phthalimides, acid fluorides, and N-(tetrafluoroaryl)phthalimides can also all be synthesized by using this method.

    4. Organocatalysis

      Organic Acid Catalysts in Reactions of Lactones with Silicon Enolates (pages 989–996)

      Dr. Hikaru Yanai, Nobuyuki Ishii, Prof. Dr. Takashi Matsumoto and Prof. Dr. Takeo Taguchi

      Article first published online: 18 SEP 2013 | DOI: 10.1002/ajoc.201300157

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      Make your choice: By choosing the organic-acid catalysts, the reaction of lactones with ketene silyl acetals results in selective formation of simple Mukaiyama aldol adducts or olefination products. That is, in the presence of acidic zwitterions, the Mukaiyama aldol adducts were selectively obtained. In contrast, the reaction in the presence of a carbon acid catalyst gave the Z-olefination products. TBS=tert-butyldimethylsilyl.

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