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Synthesis 2014; 46(14): 1901-1907
DOI: 10.1055/s-0033-1339111
DOI: 10.1055/s-0033-1339111
special topic
Nickel-Catalyzed Reductive Allylation of Ketones with Allylic Carbonates
Weitere Informationen
Publikationsverlauf
Received: 12. März 2014
Accepted after revision: 13. April 2014
Publikationsdatum:
28. Mai 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201414/lookinside/thumbnails/10.1055-s-0033-1339111-1.jpg)
Abstract
Nickel-catalyzed efficient umpolung allylation of ketones with allylic carbonates in the presence of zinc powder is developed, which accommodates a variety of allylic and ketone substrates. Although chiral ligand is necessary for the transformation, no enantioselectivity was observed.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
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For reviews on enantioselective carbonyl allylation, see:
For selected examples of asymmetric NHK reactions, see:
For selected examples of asymmetric Barbier reactions, see:
For nonasymmetric coupling of allylic alcohol/thioether with carbonyl compounds using Rh/B, see:
Rh/CO:
For Ru/CO, see:
For Ru-catalzyed reactions involving secondary alcohols, see:
For iridium-catalyzed transfer hydrogenation, see:
Allyliridium/alcohol:
For selected examples of palladium-catalyzed nonasymmetric carbonyl allylation with allylic alcohols and acetates, see: Pd/Et2Zn:
Pd(OAc)2/Et3B:
Pd/diboron via allyl–B:
Pd/SmI2:
Palladium-catalyzed asymmetric umpolung using Pd/Et2Zn:
Pd/B:
Iron-electrochemical reduction:
Fe/Mn:
For nonasymmetric coupling of allylic alcohol/thioether with carbonyl compounds using titanium-mediated protocols modulated by nickel or palladium, see:
Ti:
For nonasymmetric carbonyl allylation with allyl-OR under Ni/InI, see:
Intramolecular coupling of allyl ether with aldehyde:
For stoichiometric addition of allyl–Ni(I) to carbonyl, see:
Possible transmetalation of allylnickel with zinc: