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author:

Zhou, Ledan (Zhou, Ledan.) [1] | Liu, Ding (Liu, Ding.) [2] | Huang, Huashan (Huang, Huashan.) [3] | Zhang, Ke (Zhang, Ke.) [4] | Ning, Yingtang (Ning, Yingtang.) [5] | Chen, Fen-Er (Chen, Fen-Er.) [6]

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EI Scopus SCIE

Abstract:

We report a general approach to highly functionalized (Z)-allylic amines by decarboxylative allylation of vinyloxazolidin-2-ones. This process engages sodium sulfinates as nucleophiles to form a new carbon-sulfur bond, utilizing a palladium catalyst generated from Pd(OAc)(2) and diphosphine ligand dpppe. The scope of the protocol is illustrated by the synthesis of 30 representative allylic amines with high regio- and stereoselectivity. Mechanistic studies show that the Z-selectivity of the reaction stems from the formation of a palladacycle intermediate through Pd-N chelation. The synthetic utility of this method was further exemplified by the gram-scale synthesis and subsequent transformations to various compounds.

Keyword:

Community:

  • [ 1 ] [Zhou, Ledan]Fuzhou Univ, Coll Chem, Fuzhou 350102, Peoples R China
  • [ 2 ] [Huang, Huashan]Fuzhou Univ, Coll Chem, Fuzhou 350102, Peoples R China
  • [ 3 ] [Chen, Fen-Er]Fuzhou Univ, Coll Chem, Fuzhou 350102, Peoples R China
  • [ 4 ] [Zhou, Ledan]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 5 ] [Liu, Ding]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 6 ] [Huang, Huashan]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 7 ] [Zhang, Ke]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 8 ] [Ning, Yingtang]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 9 ] [Chen, Fen-Er]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Shanghai 200433, Peoples R China
  • [ 10 ] [Zhou, Ledan]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
  • [ 11 ] [Liu, Ding]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
  • [ 12 ] [Huang, Huashan]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
  • [ 13 ] [Zhang, Ke]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
  • [ 14 ] [Ning, Yingtang]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China
  • [ 15 ] [Chen, Fen-Er]Shanghai Engn Ctr Ind Catalysis Chiral Drugs, Shanghai 200433, Peoples R China

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Source :

CHEMICAL COMMUNICATIONS

ISSN: 1359-7345

Year: 2023

Issue: 65

Volume: 59

Page: 9892-9895

4 . 3

JCR@2023

4 . 3 0 0

JCR@2023

ESI Discipline: CHEMISTRY;

ESI HC Threshold:39

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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