Chinese Journal of Chemistry

Cover image for Vol. 30 Issue 11

Special Issue: Asymmetric Synthesis

November, 2012

Volume 30, Issue 11

Pages 2601–2725

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. You have free access to this content
      Cover Picture: The First Catalytic Asymmetric Morita-Baylis-Hillman Reaction of Acrolein with Aromatic Aldehydes (Chin. J. Chem. 11/2012) (page 2601)

      Xingping Zeng, Yunlin Liu, Congbin Ji and Jian Zhou

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201290029

      Thumbnail image of graphical abstract

      The cover picture shows the first catalytic asymmetric Morita-Baylis-Hillman (MBH) reaction of acrolein with aromatic aldehydes. Simplicity is beauty. As one of the simplest nucleophiles in MBH reaction, acrolein has never been used for the catalytic asymmetric reaction with aldehydes, although the resulting MBH adducts, with a versatile aldehyde group, are extremely useful. The Hatakeyama's catalyst β-isocupreidine, in combination with 20 mol% of 2,6-dimethoxybenzoic acid, is found to be able to catalyze the reaction of acrolein with aromatic aldehydes to give the desired MBH adducts in up to 81% ee. More details are discussed in the article by Zhou et al. on page 2631–2635.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. You have free access to this content
      Special Issue of "Asymmetric Synthesis" (page 2603)

      Shuli You

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201290030

  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. Contents: Chin. J. Chem. 11/2012 (pages 2604–2609)

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201290031

  4. Communication

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. Cu(II)-Catalyzed Enantioselective Conjugate Reduction for the Synthesis of N-Aryl β-Amino Acid Esters (pages 2611–2614)

      Yaozong Sui, Qiang Fang, Min Li, Yihu Hu, Hongfeng Xia, Shijun Li and Jing Wu

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200779

      Thumbnail image of graphical abstract

      A new set of reaction conditions has been established and allowed for the first non-noble Cu(II)-catalyzed asymmetric 1,4-hydrosilylation of N-aryl β-enamino esters under air to afford a selection of N-aryl β-amino acid esters in moderate-to-good enantiopurities (ee up to 91%).

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. One-Pot Synthesis of Pyrrolo[1,2-a]indoles by Chiral N-Triflyl Phosphoramide Catalyzed Friedel-Crafts Alkylation of 4,7-Dihydroindole with β,γ-Unsaturated α-Keto Esters (pages 2615–2623)

      Mi Zeng, Wei Zhang and Shuli You

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200759

      Thumbnail image of graphical abstract

      In the presence of 5 mol% of chiral N-triflyl phosphoramide 1a, various pyrrolo-[1,2-a]indoles were obtained in excellent enantioselectivity, moderate yields and up to 3:1 diastereoselectivity through the one-pot synthesis including the Friedel-Crafts alkylation reaction of 4,7-dihydroindole with β,γ-unsaturated α-keto esters and the subsequent p-benzoquinone oxidation.

    2. Asymmetric Aldol Reaction Catalyzed by Modularly Designed Organocatalysts (pages 2624–2630)

      Debarshi Sinha, Tanmay Mandal, Sanjib Gogoi, Joshua J. Goldman and John Cong-gui Zhao

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200639

      Thumbnail image of graphical abstract

      The direct cross aldol reactios between aldehydes and ketones were investigated with modularly designed organocatalysts (MDOs). Primary α-amino acids were found to be better reaction-center modules in this reaction.

    3. The First Catalytic Asymmetric Morita-Baylis-Hillman Reaction of Acrolein with Aromatic Aldehydes (pages 2631–2635)

      Xingping Zeng, Yunlin Liu, Congbin Ji and Jian Zhou

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201200937

      Thumbnail image of graphical abstract

      We report the first example of catalytic asymmetric Morita-Baylis-Hillman reaction of acrolein with aromatic aldehydes. The use of 10 mol% of Hatakeyama's catalyst β-isocupreidine C4, in combination with 20 mol% of 2,6-dimethoxybenzoic acid, could catalyze the reaction to give the desired products in up to 81% ee.

    4. Formation of Chiral α-Monofluorinated-β-amino Esters through Organocatalytic Asymmetric Reduction of α-Fluoro-β-enamino Esters by Trichlorosilane (pages 2636–2640)

      Peng Zhang, Chao Wang, Li Zhou and Jian Sun

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201201067

      Thumbnail image of graphical abstract

      A concise method was developed to prepare α-monofluorinated-β-amino through N-sulfinyl urea catalyzed asymmetric hydrosilylation of α-fluoro-β-enamino esters, which affords highly yields, good to high diastereoselectivities (up to >99/1) and moderate to good enantioselectivities (up to 83% ee).

    5. Enantioselective and α-Regioselective Allylic Amination of Morita-Baylis-Hillman Acetates with Simple Aromatic Amines Catalyzed by Planarly Chiral Ligand/Palladium Catalyst (pages 2641–2646)

      Yan Wang, Tao Zhang and Li Liu

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200771

      Thumbnail image of graphical abstract

      A planarly chiral ligand/palladium-catalyzed asymmetric allylic amination of Morita-Baylis-Hillman acetates with simple aromatic amines was developed in good yield with excellent α-regioselectivity (α:γ up to 30:1) and moderate enantioselectivity (up to 70% ee).

    6. Iridium-Catalyzed Allylic Alkylations of Sodium Phenyl Selenide (pages 2647–2651)

      Ruimin Cui, Xinwen Guo, Shengcai Zheng and Xiaoming Zhao

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200836

      Thumbnail image of graphical abstract

      An iridium-catalyzed allylic substitution of unsymmetrical allyl carbonates with sodium phenyl selenide was accomplished, which produced the linear allyl phenyl selenides in 38%–74% yields. The asymmetric iridium-catalyzed allylations of sodium phenyl selenide were presented as well.

    7. Enantioselective Morita-Baylis-Hillman Reaction Organocatalyzed by Glucose-based Phosphinothiourea (pages 2652–2656)

      Weihong Yang, Feng Sha, Xin Zhang, Kui Yuan and Xinyan Wu

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200740

      Thumbnail image of graphical abstract

      Chiral phosphinothiourea derived from D-glucose was developed as efficient organocatalyst for the enantioselective Morita-Baylis-Hillman reaction between acrylates and aldehydes.

    8. Stereoselective Synthesis of Optically Active Hydrobenzoins via Asymmetric Hydrogenation of Benzils with Ru(OTf)(TsDPEN)(η6-cymene) as the Pre-catalyst (pages 2657–2663)

      Xiaofei Huang, Naikai Li, Zhicong Geng, Fengfeng Pan and Xingwang Wang

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200393

      Thumbnail image of graphical abstract

      The enantioselective hydrogenation of benzils was developed by using the cationic Ru(OTf)(TsDPEN)(η6-cymene) complex as catalyst, which provided a series of enantiomerically enriched hydrobenzoins derivatives in up to 96% yield, 87:13 diastereoselectivity and >99% enantioselectivity.

    9. Ir-Catalyzed Enantioselective Hydrogenation of 2H-1,4-Benzoxazines with a Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Derived Phosphine-aminophosphine Ligand (pages 2664–2668)

      Juan Hu, Daoyong Wang, Zhuo Zheng and Xiangping Hu

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201200944

      Thumbnail image of graphical abstract

      Unsymmetrical hybrid phosphine-aminophosphine ligand derived from 1,2,3,4-tetra-hydro-1-naphthylamine has been found to be highly efficient in the Ir-catalyzed asymmetric hydrogenation of various 2H-1,4-benzoxazines, providing good enantioselectivities (up to 95% ee) and high catalytic activity (S/C up to 5000).

    10. Highly Enantioselective Michael Addition of Ketone to Alkylidene Malonates Catalyzed by Binaphthyl Sulfonimides in Water (pages 2676–2680)

      Shengjian Jia, Chunhua Luo and Daming Du

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201200910

      Thumbnail image of graphical abstract

      Binaphthyl sulfonimides have been developed to catalyze the asymmetric Michael addition of ketone to alkylidene malonates, affording the corresponging products in good to high yields (up to 98%) with good to excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (up to 92% ee) under mild conditions in water.

    11. An Efficient Asymmetric Domino Reaction of Amino Aldehyde to β,γ-Unsaturated α-Keto Esters Using trans-Perhydroindolic Acid as a Chiral Organocatalyst (pages 2681–2687)

      Jiefeng Shen, Qianjin An, Delong Liu, Yangang Liu and Wanbin Zhang

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200839

      Thumbnail image of graphical abstract

      An efficient asymmetric domino reaction of amino aldehyde to β,γ-unsaturated α-keto esters was achieved by using trans-perhydroindolic acid 1d as a chiral organocatalyst with excellent asymmetric behavior. Under the optimal reaction conditions, products with more than 99% de and up to 93% ee were obtained in high chemical yield (up to 98%) for a series of β,γ-unsaturated α-keto esters. The methodology provided an efficient route to dihydropyran derivatives containing many substituent groups (including amino groups).

    12. Enantioselective Synthesis of Terminal 1,2-Diols from Acyl Chlorides (pages 2688–2692)

      Panlin Shao, Litao Shen and Song Ye

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200697

      Thumbnail image of graphical abstract

      Chiral terminal 1,2-diols were successfully prepared in good yields with high enantiopurities by a process of cinchona alkaloids-catalyzed formal [3+2] cyclization of acyl chlorides and oxaziridine, followed by reduction.

    13. Organocatalytic Asymmetric Branching Sequence of MBH Carbonates: Access to Chiral Benzofuran-2(3H)-one Derivatives with Three Stereocenters (pages 2693–2702)

      Chuanle Zhu, Lijun Yang, Jing Nie, Yan Zheng and Junan Ma

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201200809

      Thumbnail image of graphical abstract

      An organocatalytic asymmetric branching sequence was realized in the presence of 10 mol% of (DHQD)2AQN, affording the sequential products with three stereocentres, including two quaternary carbon centres, in 47%–79% yields with 85%–99% ee.

    14. Organocatalytic Asymmetric Double Michael Reaction of Benzofuranone with Dienones to Construct Spirocyclic Benzofuranones (pages 2703–2706)

      Xiya Luo, Liangliang Wang, Lin Peng, Jianfei Bai, Lina Jia, Fang Tian, Xiaoying Xu and Lixin Wang

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200676

      Thumbnail image of graphical abstract

      The enantioselective double Michael reaction of benzofuranone with dienones catalyzed by Cinchona-based primary amines was developed. A wide range of optically active spirocyclic benzofuranones were obtained in good yields (up to 89%) and enantioselectivities (up to 91% ee).

    15. Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine (pages 2707–2713)

      Shijun Ma, Lulu Wu, Ming Liu and Yongmei Wang

      Article first published online: 14 AUG 2012 | DOI: 10.1002/cjoc.201200214

      Thumbnail image of graphical abstract

      A chiral C2-symmetric pyrrolidine-based tetraamine was synthesized from commercially starting materials, which showed good catalytic activity for asymmetric Michael additions of ketones to nitroalkenes and chalcones. The reactions proceeded smoothly to give the corresponding products in good yields (up to 99% and 91%) and in a highly selective manner (up to 91% and 93% ee) under mild conditions.

    16. A Facile Access to Fluorinated Pyrrolidines via Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Methyl α-Fluoroacrylate (pages 2714–2720)

      Dingce Yan, Qinghua Li and Chunjiang Wang

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200765

      Thumbnail image of graphical abstract

      Asymmetric 1,3-dipolar cycloaddition of methyl α-fluoroacrylate with azomethine ylides for the construction of optically active fluorinated pyrrolidines bearing one unique fluorinated quaternary and two tertiary stereogenic centers has been achieved with Cu(CH3CN)4BF4/TF-BiphamPhos complexes for the first time. This catalytic system performs well over a broad scope of substrates, providing the synthetically useful adducts in high yields and excellent diastereoselectivities and good to high enantioselectivities.

  6. Note

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    1. Organocatalytic Enantioselective Dehydrogenative α-Alkylation of Aldehydes with Benzylic Compounds (pages 2721–2725)

      Fen Huang, Lubin Xu and Jian Xiao

      Article first published online: 15 NOV 2012 | DOI: 10.1002/cjoc.201200850

      Thumbnail image of graphical abstract

      The highly enantioselective cross-dehydrogenative coupling of aldehydes with benzylic compounds has been developed as an efficient and rapid protocol for synthesis of enantioriched α-alkylated aldehydes.

SEARCH

SEARCH BY CITATION