AN EFFICIENT BUTENOLIDE ANNULATION VIA ALPHA'-CHLOROACETOXYLATION OF ENONES USING MANGANESE(III) ACETATE AND CHLOROACETIC ACID

Date

1991-09-01

Author

DEMIR, AS
AKGUN, H
Tanyeli, Cihangir
SAYRAC, T
WATT, DS

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The alpha'-chloroacetoxylation of alpha,-beta-unsaturated ketones using manganese(III) acetate and chloroacetic acid followed by Arbuzov reaction and intramolecular Horner-Emmons olefination provided a convenient synthesis of annulated 2-buten-4-olides.

Subject Keywords

CARBOXYLIC-ACIDS, FURAN SYNTHESIS, COMBINATION, DERIVATIVES, OXIDATION

URI

https://hdl.handle.net/11511/52650

Journal

SYNTHESIS-STUTTGART

Collections

Department of Chemistry, Article

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A facile synthesis of various butenolides Tanyeli, Cihangir (Informa UK Limited, 2000-01-01) The synthesis of alpha'-acyloxy-alpha,beta-unsaturated cyclic ketones from the corresponding alpha,beta-unsaturated cyclic ketones by using manganese (III) acetate in combination with 2-chloropropionic acid followed by subsequent Arbuzov and intramolecular Horner-Emmons cyclization reactions provided a convenient synthetic pathway to various butenolides 4a-d.
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.
AN EFFICIENT SYNTHESIS OF SUBSTITUTED 2H-PYRAN-2-ONE DERIVATIVES VIA THE CONJUGATED ADDITION OF THE ENOLATES OF CARBONYL-COMPOUNDS TO ENAMINOESTERS DEMIR, AS; Tanyeli, Cihangir; URKMEZKARAASLAN, R; SAYRAC, T (Informa UK Limited, 1991-01-01) Short simple synthesis of alkenoic acid esters and their intramolecular cyclization products, 2H-Pyran-2-ones from enolates of carbonyl compounds and enaminoesters are described.
THE ALPHA'-OXIDATION OF ALPHA-ALKOXY ENONES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS Demir, Ayhan Sıtkı; SAATCIOGLU, A (Informa UK Limited, 1993-01-01) The alpha'-oxidation of cyclic derivatives of alpha-alkoxy-alpha,beta-unsaturated ketones using manganese(III)acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-2-alkoxy-2-cyclopentenones and 6-acyloxy-2-alkoxy-2-cyclohexenones.
A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives BOLM, CARSTEN; SCHİFFERS, INGO; ATODİRESEİ, IULİANA; Özçubukçu, Salih; RAABE, GERHARD (Royal Society of Chemistry (RSC), 2003-01-01) The simple and highly enantioselective methanolysis of norbornene dicarboxylic acid anhydride mediated by quinidine leads to the corresponding cis-monomethyl ester with 98% ee. By means of selective ester epimerization, followed by Curtius degradation of the intermediate trans-diacyl azide, two optically active norbornane-type diamines are obtained as their hydrochloric salts. Liberating the amine with an excess of triethylamine in situ and subsequent derivatization affords potential C-1-symmetric ligands f...

Citation Formats

A. DEMIR, H. AKGUN, C. Tanyeli, T. SAYRAC, and D. WATT, “AN EFFICIENT BUTENOLIDE ANNULATION VIA ALPHA’-CHLOROACETOXYLATION OF ENONES USING MANGANESE(III) ACETATE AND CHLOROACETIC ACID,” SYNTHESIS-STUTTGART, pp. 719–721, 1991, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/52650.