Copper-Catalyzed Enantioselective Synthesis of Oxazolines from Aminotriols via Asymmetric Desymmetrization

被引：15
|
作者：
Yamamoto, Kosuke [1 ]
Tsuda, Yutaro [1 ]
Kuriyama, Masami [1 ]
Demizu, Yosuke [1 ]
Onomura, Osamu [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2020年 / 15卷 / 06期
基金：
日本学术振兴会;
关键词：
copper; asymmetric synthesis; alpha-tertiary amines; triols; oxazolines; TRIS ALPHA; ALPHA; ALPHA-TRIMETHYLOLAMINOMETHANE; STEREOSELECTIVE-SYNTHESIS; AMINOPOLYOLS SKELETON; BIOLOGICAL EVALUATION; KINETIC RESOLUTION; CHIRAL OXAZOLINES; RECENT PROGRESS; AMINO-ACIDS; DERIVATIVES; LIGANDS;
D O I：
10.1002/asia.201901742
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A copper-catalyzed enantioselective transformation of tris(hydroxymethyl)aminomethane-derived aminotriols was developed to provide multisubstituted oxazolines with a tetrasubstituted carbon center. The present transformation consisted of sequential reactions involving mono-sulfonylation of aminotriols, subsequent intramolecular cyclization to afford prochiral oxazoline diols, and sulfonylative asymmetric desymmetrization of resultant oxazoline diols. In addition, the kinetic resolution process would be involved in the sulfonylative asymmetric desymmetrization step, which would amplify the enantiopurities of the desired products. Various aminotriols were tolerated in the present reaction, affording the desired oxazolines in good to high yields with excellent enantioselectivities. The synthetic utility of the present reaction was demonstrated by the transformation of the optically active oxazoline into a chiral alpha-tertiary amine motif.
引用
收藏
页码：840 / 844
页数：5
相关论文
共 50 条
  • [31] Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay
    Fu, Liang
    Zhou, Song
    Wan, Xiaolong
    Chen, Pinhong
    Liu, Guosheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (35) : 10965 - 10969
  • [32] Copper-Catalyzed Enantioselective Difluoromethylation of Amino Acids via Difluorocarbene
    Peng, Lingzi
    Wang, Hongyi
    Guo, Chang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6376 - 6381
  • [33] Chiral amides via copper-catalyzed enantioselective conjugate addition
    Schoonen, Anne K.
    Fernandez-Ibanez, Maria A.
    Fananas-Mastral, Martin
    Teichert, Johannes F.
    Feringa, Ben L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [34] Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay
    Liu, Guosheng (gliu@mail.sioc.ac.cn), 1600, American Chemical Society (140):
  • [35] Enantioselective Arylcyanation of Styrenes via Copper-Catalyzed Radical Relay†
    Zhuang, Weiwen
    Chen, Pinhong
    Liu, Guosheng
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (01): : 50 - 54
  • [36] Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination
    Ichikawa, Saki
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2019, 21 (21) : 8736 - 8739
  • [37] Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols
    Karyakarte, Shuklendu D.
    Um, Chanchamnan
    Berhane, Ilyas A.
    Chemler, Sherry R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12921 - 12924
  • [38] Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers
    Chen, Dake
    Berhane, Ilyas A.
    Chemler, Sherry R.
    ORGANIC LETTERS, 2020, 22 (19) : 7409 - 7414
  • [39] Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines
    Koradin, C
    Polborn, K
    Knochel, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (14) : 2535 - +
  • [40] Enantioselective formal synthesis of (+)-precapnelladiene by chiral copper-catalyzed asymmetric [2+2]-cycloaddition reaction
    Takenaka, Yosuke
    Ito, Hisanaka
    Iguchi, Kazuo
    TETRAHEDRON, 2007, 63 (02) : 510 - 513
12345