Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives

Date

1997-03-13

Author

Demir, Ayhan Sıtkı
Akhmedov, Idris M.
Tanyeli, Cihangir
GERÇEK, Zuhal
Gadzhili, Raik A.

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5-Chloro-3-penten-2-one reacts with the amino group of homochiral amines, amino alcohols, amino acid esters to form corresponding 2-pyrrole derivatives in good yield and without racemization. (C) 1997 Elsevier Science Ltd.

Subject Keywords

Protecting group

URI

https://hdl.handle.net/11511/41136

Journal

Tetrahedron Asymmetry

DOI

https://doi.org/10.1016/s0957-4166(97)00035-9

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Department of Chemistry, Article

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Conversion of homochiral amines, beta-amino alcohols and alpha-amino acids to their chiral 2-substituted pyrrole derivatives Demir, Ayhan Sıtkı; Akhmedov, IM; Sesenoglu, O; Alpturk, O; Apaydin, S; Gercek, Z; Ibrahimzade, N (2001-01-01) The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters
OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID DEMIR, AS; CAMKERTEN, N; AKGUN, H; Tanyeli, Cihangir; MAHASNEH, AS; WATT, DS (Informa UK Limited, 1990-01-01) The α-oxidation of aryl alkyl ketones using manganese(III) acetate in the presence of various carboxylic acids and (1S)-(+)-10-camphorsulfonic acid provided a convenient synthesis of α-acyloxy, α-(10-camphorsulfonyloxy), and α-hydroxy derivatives in good yield.
Synthesis of 1,2,3,5- tetrasubstituted pyrrole derivatives via 5-exo-dig type cyclization and stereoselective functionalisation of ferrocene derivatives Kayalar, Metin; Demir, Ayhan Sıtkı; Department of Chemistry (2005) A convenient and new method for the synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives starting from 1,3,-dicarbonyl compounds through acid catalyzed cyclization reaction is described. Alkylation of 1,3-dicarbonyl compound with propargyl bromide followed by one step cyclization with the introduction of primary amines in the presence of catalytic amount of triflouroacetic acid (TFA) affords the corresponding pyrrole derivatives in high yields. The investigations on the studies of developing a new meth...
Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones Demir, Ayhan Sıtkı; Aybey, Asuman (Elsevier BV, 2008-12-01) The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords ph...
THE OXIDATION OF BETA-ALKOXYCYCLOPENTENONES AND BETA-ALKOXYCYCLOHEXENONES TO ALPHA'-ACYLOXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS Demir, Ayhan Sıtkı; SAYRAC, T; WATT, DS (1990-12-01) The alpha-oxidation of cyclic derivatives of beta-alkoxy-alpha, beta-unsaturated ketones using manganese (III) acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-3-alkoxy-2-cyclopentenones and 6-acyloxy-3-alkoxy-2-cyclohexenones.

Citation Formats

A. S. Demir, I. M. Akhmedov, C. Tanyeli, Z. GERÇEK, and R. A. Gadzhili, “Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-methylpyrrole derivatives,” Tetrahedron Asymmetry, pp. 753–757, 1997, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/41136.