Catalytic Asymmetric Synthesis of Isochroman Derivatives

被引:20
|
作者
Tamanna [1 ]
Kumar, Mukesh [2 ]
Joshi, Kavita [1 ]
Chauhan, Pankaj [1 ]
机构
[1] Indian Inst Technol Jammu Jagti, Dept Chem, NH 44, Jammu 181221, Jammu & Kashmir, India
[2] Sahu Jain Coll, Dept Chem, Najibabad 246763, Bijnor, India
关键词
asymmetric catalysis; isochromanones; isochromans; isochromenes; organic catalysis; OXA-MICHAEL REACTION; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; BRONSTED ACID; DIASTEREOSELECTIVE SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; CARBOXYLIC-ACIDS; BENZYLIC ETHERS; CONSTITUENTS; HYDRANGENOL;
D O I
10.1002/adsc.202000243
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The isochroman scaffold constitutes an important structural unit, which is present in various bioactive natural products and synthetic pharmaceutical compounds exhibiting wide arrays of biological properties. Hence the synthesis of this class of heterocyclic compounds in a stereoselective fashion is highly significant and desirable. In the last decade, a substantial advancement has been witnessed ln the catalytic asymmetric synthesis of isochroman derivatives by employing metal catalysts bearing chiral ligands or by chiral metal-free organocatalysts. This review aims to provide an overview of the transition metal-catalyzed and organocatalyzed asymmetric syntheses of isochroman derivatives including isochromenes and isochromanones.
引用
收藏
页码:1907 / 1926
页数:20
相关论文
共 50 条
  • [41] Catalytic asymmetric synthesis of cyclohexylnorstatine
    Pasto, M
    Castejon, P
    Moyano, A
    Pericas, MA
    Riera, A
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17): : 6033 - 6037
  • [42] Catalytic, asymmetric synthesis of siphonarienal
    Calter, MA
    Liao, WS
    Struss, JA
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22): : 7500 - 7504
  • [43] STUDIES IN THE ISOCHROMAN AND ISOTHIOCHROMAN SERIES .23. FORMYLATION OF ISOCHROMAN, ISOTHIOCHROMAN, AND THEIR DERIVATIVES
    BOHME, H
    SUTOYO, PN
    LIEBIGS ANNALEN DER CHEMIE, 1982, (09): : 1643 - 1655
  • [44] Synthesis of an isochroman analogue of the michellamines
    de Koning, CB
    Michael, JP
    van Otterlo, WAL
    TETRAHEDRON LETTERS, 1999, 40 (15) : 3037 - 3040
  • [46] Catalytic Asymmetric Homologation of α-Ketoesters with α-Diazoesters: Synthesis of Succinate Derivatives with Chiral Quaternary Centers
    Li, Wei
    Liu, Xiaohua
    Tan, Fei
    Hao, Xiaoyu
    Zheng, Jianfeng
    Lin, Lili
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (41) : 10883 - 10886
  • [47] Catalytic asymmetric synthesis of pyrrolidine derivatives bearing heteroatom-substituted quaternary stereocenters
    Wang, Zhi-Peng
    Wu, Qi
    Jiang, Jia
    Li, Zi-Rui
    Peng, Xiao-Jiao
    Shao, Pan-Lin
    He, Yun
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01): : 36 - 40
  • [48] Catalytic stereoselective synthesis of alpha-amino phosphonic acid derivatives by asymmetric hydrogenation
    Schmidt, U
    Oehme, G
    Krause, H
    SYNTHETIC COMMUNICATIONS, 1996, 26 (04) : 777 - 781
  • [49] Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes
    Arae, Sachie
    Beppu, Shota
    Kawatsu, Takahiro
    Igawa, Kazunobu
    Tomooka, Katsuhiko
    Irie, Ryo
    ORGANIC LETTERS, 2018, 20 (16) : 4796 - 4800
  • [50] Catalytic Asymmetric Cycloaddition of Ketenes and Nitroso Compounds: Enantioselective Synthesis of α-Hydroxycarboxylic Acid Derivatives
    Dochnahl, Maximilian
    Fu, Gregory C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) : 2391 - 2393