Convenient route to 2-(trialkylstannyl)cyclopropylamines and their application in palladium-catalyzed cross-coupling reactions

Wiedemann, Stefan, Rauch, Karsten, Savchenko, Andrei, Marek, Ilan and de Meijerreactions, Armin (2004) Convenient route to 2-(trialkylstannyl)cyclopropylamines and their application in palladium-catalyzed cross-coupling reactions. European Journal of Organic Chemistry, 2004 3: 631-635. doi:10.1002/ejoc.200300454


Author Wiedemann, Stefan
Rauch, Karsten
Savchenko, Andrei
Marek, Ilan
de Meijerreactions, Armin
Title Convenient route to 2-(trialkylstannyl)cyclopropylamines and their application in palladium-catalyzed cross-coupling reactions
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1434-193X
1099-0690
Publication date 2004
Sub-type Article (original research)
DOI 10.1002/ejoc.200300454
Volume 2004
Issue 3
Start page 631
End page 635
Total pages 5
Place of publication Weinheim, Germany
Publisher Wiley-VCH Verlag GmbH; KGaA
Language eng
Subject 0305 Organic Chemistry
Formatted abstract
The 2-(trialkylstannyl)-N,N-dialkylcyclopropylamines 3 were obtained by titanium-mediated aminocyclopropanation of tributylvinylstannane with N,N-dialkylformamides in yields of 80-84% and with excellent diastereoselectivities (trans/cis > 45:1). The resulting stannanes could advantageously be applied in Stille cross-coupling reactions with aryl iodides, providing the pure trans-2-aryl-(N,N-dialkylamino)cyclopropanes 8 in yields ranging from 45 to 67% (six examples). The coupling of ethyl (E)-3-iodoacrylate (9) gave ethyl cis-5-(dibenzylamino)cyclopent-2-enecarboxylate (10) as a single diastereomer in 54% yield.
Keyword Cross-coupling
Rearrangement
Small ring systems
Tin
Titanium
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Australian Institute for Bioengineering and Nanotechnology Publications
 
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Created: Fri, 08 Jan 2010, 14:41:26 EST by Elissa Saffery on behalf of Aust Institute for Bioengineering & Nanotechnology