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  4. Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones
 
research article

Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones

Benfatti, Fides  
•
de Nanteuil, Florian  
•
Waser, Jerome  
2012
Chemistry - A European Journal

The first enantiospecific [3+2] annulation of D-A amino-cyclopropanes with ketones is reported herein (see scheme; Phth = phthaloyl). The reaction is catalyzed by 5 mol % of tin(IV) chloride at -78 °C and gives aminotetra-hydrofurans bearing a C5-quaternary stereocenter in high yield, diastereoselectivity and enantio-specificity.

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Type
research article
DOI
10.1002/chem.201103971
Web of Science ID

WOS:000302354500008

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

2012

Published in
Chemistry - A European Journal
Volume

18

Start page

4844

End page

4849

Subjects

annulation

•

aminotetrahydrofuran

•

catalysis

•

D-A aminocyclopropane

•

enantiospecificity

•

ketones

•

Donor-Acceptor Cyclopropanes

•

Ring-Expansion Reaction

•

Carbonyl-Compounds

•

Substituted Cyclopropanes

•

2

•

2-Dialkoxycyclopropanecarboxylic Esters

•

Organic-Synthesis

•

Stereoselective-Synthesis

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSO  
Available on Infoscience
May 4, 2012
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/80019
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