Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. Journal articles
  4. Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct
 
research article

Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct

Zhang, Yun
•
Ao, Yu-Fei
•
Huang, Zhi-Tang
Show more
2016
Angewandte Chemie International Edition

Reaction of isonitriles with 3-(arylamino)isobenzofuran-1(3H)-ones in the presence of a catalytic amount of an octahydro (R)-binol-derived chiral phosphoric acid afforded 3-oxo-2-arylisoindoline-1-carboxamides in high yields with good to high enantioselectivities. An enantioselective Ugi fourcenter three-component reaction of 2-formylbenzoic acids, anilines, and isonitriles was subsequently developed for the synthesis of the same heterocycle. Mechanistic studies indicate that the enantioselectivity results from the dynamic kinetic resolution of the primary Ugi adduct, rather than from the C-C bond-forming process. The resulting heterocycle products are of significant medicinal importance.

  • Details
  • Metrics
Type
research article
DOI
10.1002/anie.201600751
Web of Science ID

WOS:000374564300029

Author(s)
Zhang, Yun
Ao, Yu-Fei
Huang, Zhi-Tang
Wang, De-Xian
Wang, Mei-Xiang
Zhu, Jieping  
Date Issued

2016

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

55

Issue

17

Start page

5282

End page

5285

Subjects

asymmetric synthesis

•

kinetic resolution

•

multicomponent reactions

•

organocatalysis

•

reaction mechanisms

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
April 22, 2016
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/125849
Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés