Mn(III) acetate-mediated regioselective benzylation of various alpha,beta-unsaturated and beta-alkoxy-alpha,beta-unsaturated ketones

Date

2003-09-22

Author

Tanyeli, Cihangir

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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.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/38693

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2003.08.001

Collections

Department of Chemistry, Article

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Mn(III)-based C-C bond formation: regioselective alpha '-allylation of various alpha,beta-unsaturated, alpha and beta-alkoxy alpha,beta-unsaturated ketones Tanyeli, Cihangir (Elsevier BV, 2005-08-22) 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 alph...
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.
Manganese(III) acetate promoted acetoxylation of various α,β-unsaturated cyclopentanones Tanyeli, Cihangir; Turkut, Engin; SEZEN, Bengü (Elsevier BV, 2003-02-10) We describe the results of manganese(III) acetate based regioselective oxidation of various alpha,beta-unsaturated cyclopentanones leading to alpha'-acetoxy alpha,beta-unsaturated cyclopentanones in good yields. Products due to monophenyl and diphenyl substituted dimerization have been identified as byproducts of the reaction.
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.
Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds Demir, Ayhan Sıtkı; Akhmedov, IM; Sesenoglu, O (Elsevier BV, 2002-12-02) 2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.

Citation Formats

C. Tanyeli, “Mn(III) acetate-mediated regioselective benzylation of various alpha,beta-unsaturated and beta-alkoxy-alpha,beta-unsaturated ketones,” TETRAHEDRON LETTERS, pp. 7311–7313, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/38693.