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  4. Cinchona Alkaloid-Amides Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Enantioselective Synthesis of 2,4-Substituted Azetidines
 
research article

Cinchona Alkaloid-Amides Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Enantioselective Synthesis of 2,4-Substituted Azetidines

Denis, Jean-Baptiste
•
Masson, Géraldine
•
Retailleau, Pascal
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2011
Angewandte Chemie International Edition

Mix and go. The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines (2) and alkyl 2,3-butadienoate (3) afforded the (R)-azetidines 4 in excellent yields and enantioselectivities. The (S)-enantiomer was obtained when a quinine-amide catalyst, the pseudoenantiomer of (1) was used.

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Type
research article
DOI
10.1002/anie.201100706
Web of Science ID

WOS:000291953200023

Author(s)
Denis, Jean-Baptiste
Masson, Géraldine
Retailleau, Pascal
Zhu, Jieping  
Date Issued

2011

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

50

Issue

23

Start page

5356

End page

5360

Subjects

allenoates

•

asymmetric synthesis

•

cycloaddition

•

nitrogen heterocycles

•

organocatalysis

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
May 31, 2011
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/68068
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