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Author:

Zhao, Hong-Wu (Zhao, Hong-Wu.) | Li, Hai-Long (Li, Hai-Long.) | Yue, Yuan-Yuan (Yue, Yuan-Yuan.) | Sheng, Zhui-Hui (Sheng, Zhui-Hui.)

Indexed by:

Scopus SCIE

Abstract:

A new class of axially-unfixed biaryl-based pyrrolidines with C-2-symmetry were designed and synthesized by using enantiopure alpha-proline as a chiral source. These bifunctional organocatalys provided Michael adducts in high chemical yields (up to 99%) and with excellent stereoselectivities (up to 99: 1 dr and 96% ee) in the direct Michael addition reactions of a variety of ketones and aldehydes to nitro olefins. The transition states were proposed to clarify the stereochemical course of the examined reactions.

Keyword:

Nitrogen heterocycles Diastereoselectivity Michael addition Enantioselectivity Synthetic methods Organocatalysis C-C coupling

Author Community:

  • [ 1 ] [Zhao, Hong-Wu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 2 ] [Li, Hai-Long]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 3 ] [Yue, Yuan-Yuan]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 4 ] [Sheng, Zhui-Hui]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: 2013

Issue: 9

Volume: 2013

Page: 1740-1748

2 . 8 0 0

JCR@2022

ESI Discipline: CHEMISTRY;

JCR Journal Grade:1

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count: 26

SCOPUS Cited Count: 30

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 10

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