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  4. Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans
 
research article

Iron-Catalyzed [3+2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans

Benfatti, Fides  
•
de Nanteuil, Florian  
•
Waser, Jerome  
2012
Organic Letters

The first method for the [3 + 2] annulation of donor acceptor aminocyclopropanes with aldehydes is reported. The reaction is catalyzed by iron trichlorlde on alumina in yields up to 99% and with excellent cis selectivities (up to >20:1) and represents a stereoselective and atom economic access to valuable 2-aminotetrahydrofurans, which constitute the core of DNA and RNA.

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Type
research article
DOI
10.1021/ol203144v
Web of Science ID

WOS:000298828500099

Author(s)
Benfatti, Fides  
de Nanteuil, Florian  
Waser, Jerome  
Date Issued

2012

Publisher

American Chemical Society

Published in
Organic Letters
Volume

14

Start page

386

End page

389

Subjects

Donor-Acceptor Cyclopropanes

•

Aldol-Type Reaction

•

Ring-Expansion Reaction

•

Carbonyl-Compounds

•

2

•

2-Dialkoxycyclopropanecarboxylic Esters

•

Diastereoselective Synthesis

•

Organic-Synthesis

•

Annulation

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSO  
Available on Infoscience
February 23, 2012
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/78062
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