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Author:

Zhao, Hong-Wu (Zhao, Hong-Wu.) | Li, Bo (Li, Bo.) | Tian, Ting (Tian, Ting.) | Meng, Wei (Meng, Wei.) | Yang, Zhao (Yang, Zhao.) | Song, Xiu-Qing (Song, Xiu-Qing.) | Chen, Xiao-Qin (Chen, Xiao-Qin.) | Pang, Hai-Liang (Pang, Hai-Liang.)

Indexed by:

Scopus SCIE

Abstract:

In the presence of cinchona-thiourea organocatalyst C1, the developed organocatalytic three-component cascade reaction of isatins, malononitrile, and 2-hydroxynaphthalene-1,4-diones readily proceeded to furnish chiral pyranonaphthoquinone-fused spirooxindoles in excellent chemical yields and high enantioselectivities (up to 99% yield and 97%ee). The absolute configurations of the spirooxindoles were assigned on the basis of an X-ray single crystal structure. Moreover, a reaction mechanism is proposed that accounts for the stereocontrolled formation of the chiral spirooxindoles,.

Keyword:

Spiro compounds Multicomponent reactions Enantioselectivity Domino reactions Organocatalysis Asymmetric catalysis

Author Community:

  • [ 1 ] [Zhao, Hong-Wu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 2 ] [Li, Bo]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 3 ] [Tian, Ting]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 4 ] [Meng, Wei]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 5 ] [Yang, Zhao]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 6 ] [Song, Xiu-Qing]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 7 ] [Chen, Xiao-Qin]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 8 ] [Pang, Hai-Liang]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

Reprint Author's Address:

  • [Zhao, Hong-Wu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

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Source :

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

ISSN: 1434-193X

Year: 2015

Issue: 15

Volume: 2015

Page: 3320-3326

2 . 8 0 0

JCR@2022

ESI Discipline: CHEMISTRY;

ESI HC Threshold:253

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count: 29

SCOPUS Cited Count: 34

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 8

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