Copper Catalyzed One-Pot Three-Component Imination-Alkynylation-aza-Michael Sequence: Enantio- and Diastereoselective Syntheses of 1,3-Disubstituted Isoindolines and Tetrahydroisoquinolines

被引：21
|
作者：
Das, Braja Gopal [1 ]
Shah, Sadhna [1 ]
Singh, Vinod K. [1 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 13期
关键词：
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CYCLIZATION; CONSTRUCTION; PAZINACLONE; CHEMISTRY; ACCESS; MODE;
D O I：
10.1021/acs.orglett.9b01507
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantio- and diastereoselective syntheses of 1, 3-disubstituted isoindolines and tetrahydroisoquinolines via Cu-I -Pybox-diPh catalyzed one-pot imination-alkynylation-aza-Michael sequence has been reported. The three-component reaction produces one C-C and two C-N bonds sequentially with high yield (up to 92%), enantioselectivity (up to 99%), and diastereoselectivity (up to 9:1) in a single operation. Furthermore, the synthetic utility of the product has been demonstrated by LiAlH4 reduction of ester and hydrogenation of alkyne functionality without losing the stereoselectivity.
引用
收藏
页码：4981 / 4985
页数：5
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  • [1] Enantio- and Diastereoselective Betti/aza-Michael Sequence: Single Operated Preparation of Chiral 1,3-Disubstituted Isoindolines
    Takizawa, Shinobu
    Sako, Makoto
    Abozeid, Mohamed Ahmed
    Kishi, Kenta
    Wathsala, H. D. P.
    Hirata, Shuichi
    Murai, Kenichi
    Fujioka, Hiromichi
    Sasai, Hiroaki
    [J]. ORGANIC LETTERS, 2017, 19 (19) : 5426 - 5429
  • [2] Bronsted acid catalyzed enantio- and diastereoselective one-pot three component Mannich reaction
    Barbero, Margherita
    Cadamuro, Silvano
    Dughera, Stefano
    [J]. TETRAHEDRON-ASYMMETRY, 2015, 26 (20) : 1180 - 1188
  • [3] Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins
    Olimpieri, Francesca
    Volonterio, Alessandro
    Zanda, Matteo
    [J]. SYNLETT, 2008, (19) : 3016 - 3020
  • [4] A One-Pot, Three-Component Approach to Functionalised Tetrahydroisoquinolines Using Domino Heck-aza-Michael Reactions
    Priebbenow, Daniel L.
    Pfeffer, Frederick M.
    Stewart, Scott G.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1632 - 1635
  • [5] Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes
    Sawano, Eri
    Ogasawara, Masamichi
    [J]. ACS OMEGA, 2019, 4 (21): : 19499 - 19504
  • [6] Copper-Catalyzed One-Pot Three-Component Aminophosphinoylation of 1,4-Naphthoquinone
    Wang, Bin
    Han, Wancang
    Zhang, Yonghong
    Chen, Ziren
    Xia, Yu
    Wu, Shaofeng
    Xue, Fei
    Jin, Weiwei
    Liu, Chenjiang
    [J]. CHEMISTRYSELECT, 2024, 9 (27):
  • [7] Copper-catalyzed one-pot three-component thioamination of 1,4-naphthoquinone
    Zeng, Fan-Lin
    Chen, Xiao-Lan
    He, Shuai-Qi
    Sun, Kai
    Liu, Yan
    Fu, Rui
    Qu, Ling-Bo
    Zhao, Yu-Fen
    Yu, Bing
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (09): : 1476 - 1480
  • [8] DBSA catalyzed, one-pot three-component "on water" green protocol for the synthesis of 2,3-disubstituted 4-thiazolidinones
    Prasad, Davinder
    Preetam, Amreeta
    Nath, Mahendra
    [J]. RSC ADVANCES, 2012, 2 (07) : 3133 - 3140
  • [9] Nickel-Catalyzed Enantio- and Diastereoselective Three-Component Coupling of 1,3-Dienes, Aldehydes, and a Silylborane Leading to a-Chiral Allylsilanes
    Saito, Nozomi
    Kobayashi, Ayami
    Sato, Yoshihiro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (05) : 1228 - 1231
  • [10] A one-pot, three-component and solvent-free synthesis of 2,3-disubstituted isoindolin-1-ones
    Adib, Mehdi
    Peytam, Fariba
    Zainali, Mohsen
    Zhu, Long-Guan
    Wu, Jing
    [J]. TETRAHEDRON LETTERS, 2015, 56 (33) : 4729 - 4732
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