Title
Directed ruthenium-catalyzed <tex>$C(sp^{3})$</tex> -H <tex>$\alpha$</tex>-alkylation of cyclic amines using dioxolane-protected alkenones Directed ruthenium-catalyzed <tex>$C(sp^{3})$</tex> -H <tex>$\alpha$</tex>-alkylation of cyclic amines using dioxolane-protected alkenones
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
Advanced synthesis and catalysis. - Weinheim
Volume/pages
356(2014) :7 , p. 1610-1618
ISSN
1615-4150
ISI
000336505000026
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
A catalytic system for ruthenium-catalyzed C(sp3)[BOND]H α-alkylation of piperidines with dioxolane-protected alkenones is reported. Dioxolane protection of the ketone proved crucial to obtain alkylation products. A diverse set of highly substituted piperidines was readily prepared in moderate to good yields via this methodology from easily accessible starting materials (C-2, C-3 and C-4 substituted piperidines). When the methodology is applied to C-3 substituted piperidines, featuring two α positions, only monoalkylated products (2,5-disubstituted) are observed. Even bicyclic amines, which feature a fused piperidine moiety, can be used. The successful directing group as well as protecting group (ketal) removal is also demonstrated. The methodology thus allows one to further derivatize and access hitherto unknown functionalized cyclic amine derivatives and will be useful in molecular library synthesis.
E-info
https://repository.uantwerpen.be/docman/iruaauth/8c94d0/dbd145d9982.pdf
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000336505000026&DestLinkType=RelatedRecords&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000336505000026&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000336505000026&DestLinkType=CitingArticles&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
Handle