Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Mn(III)-based C-C bond formation: regioselective alpha '-allylation of various alpha,beta-unsaturated, alpha and beta-alkoxy alpha,beta-unsaturated ketones
Date
2005-08-22
Author
Tanyeli, Cihangir
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
64
views
0
downloads
Cite This
The Manganese(III) -based regioselective alpha'-keto radical generation of unsaturated ketones is a versatile synthetic procedure with broad applicability. The generated alpha'-keto radical slowly creates a metal enolate in a solvent at reflux. The resultant metal enolate affords the corresponding alpha'-allylated alpha,beta-unsaturated ketones in good yields. This method is the first example of the metal mediated regioselective alpha'-allylation of alpha,beta-unsaturated ketones. The ketones that have alpha or beta-alkoxy groups also work efficiently.
Subject Keywords
Organic Chemistry
,
Biochemistry
,
Drug Discovery
URI
https://hdl.handle.net/11511/42893
Journal
TETRAHEDRON
DOI
https://doi.org/10.1016/j.tet.2005.06.031
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
Asymmetric aldol addition of alpha-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst
Okumus, Seda; Tanyeli, Cihangir; Demir, Ayhan Sıtkı (Elsevier BV, 2014-07-30)
The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of alpha-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synthons with enantioselectivities of up to 91:9 and enriched diastereoselectivities of up to 95:5 (syn:anti).
Reinvestigation of the synthetic and mechanistic aspects of Mn(III) acetate mediated oxidation of enones
Demir, Ayhan Sıtkı; Reis, O; Igdir, AC (Elsevier BV, 2004-04-05)
Mn(OAc)(3) mediated alpha'-acetoxylation of alpha,beta-unsaturated enones is reinvestigated from a synthetic and mechanistic point of view and an improved procedure based on the use of acetic acid as a co-solvent is presented. Excellent results were obtained for a variety of structurally diverse and synthetically important enones under the optimized conditions.
Mn(III) acetate-mediated regioselective benzylation of various alpha,beta-unsaturated and beta-alkoxy-alpha,beta-unsaturated ketones
Tanyeli, Cihangir (Elsevier BV, 2003-09-22)
We describe herein the results of manganese(III) acetate mediated alpha'-benzylation of various a,p-unsaturated and beta-alkoxy-alpha,beta-unsaturated ketones in moderate yields.
Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes
Vatansever, Erol Can; Kilic, Kubra; Ozer, Merve Sinem; KOZA, GANİ; Menges, Nurettin; Balcı, Metin (Elsevier BV, 2015-09-30)
A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap.
Manganese(III) acetate based tandem oxidation of various α and β-alkoxy α,β-unsaturated ketones
Tanyeli, Cihangir; Sezen, Bengü (Elsevier BV, 2002-12-09)
We described the unusual results of manganese(III) acetate based tandem oxidation of various alpha and beta-alkoxy alpha,beta-unsaturated ketones to afford the corresponding alpha'-acetoxy-alpha'-phenyl substituted oxidation products in good yields. The tandem oxidation to monoacetoxylation ratio can be tuned by the amount of manganese(III) acetate.
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
C. Tanyeli, “Mn(III)-based C-C bond formation: regioselective alpha ’-allylation of various alpha,beta-unsaturated, alpha and beta-alkoxy alpha,beta-unsaturated ketones,”
TETRAHEDRON
, pp. 8212–8217, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42893.