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  4. Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
 
research article

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

Buyck, Thomas  
•
Pasche, Delphine
•
Wang, Qian  
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2016
Chemistry - A European Journal

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3-dipole. The phenylselenonyl group played a triple role as an electron-withdrawing group to activate the 1,4-addition, a leaving group, and a latent oxidant in this transformation.

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Type
research article
DOI
10.1002/chem.201505050
Web of Science ID

WOS:000369855000013

Author(s)
Buyck, Thomas  
Pasche, Delphine
Wang, Qian  
Zhu, Jieping  
Date Issued

2016

Publisher

Wiley-Blackwell

Published in
Chemistry - A European Journal
Volume

22

Issue

7

Start page

2278

End page

2281

Subjects

annulation

•

domino reactions

•

isocyanide

•

oxazolidinone

•

selenium

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
February 16, 2016
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/124253
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