Reactions of diethylaluminum cyanide with acyl phosphonates

Sevim, İlhan
This thesis includes reaction of diethylaluminum cyanide with acyl phosphonates. Cyanohidrin O-phosphates are synthesized from easily available acyl phosphonates and diethylaluminum cyanide. Synthesis of cross-benzoin product of acyl phosphonate, α-hydroxy phosphonate and tertiary carbinol are synthesized from the reaction of diethylaluminum cyanide with acyl phosphonates, representatively. Asymmetric syntheses of cyanohydrin and benzoin type reaction of acyl phoshonate are also investigated representatively.


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Sudemen, Mahir Burak; ZENGİN, MUSTAFA; GENÇ, HAYRİYE; Balcı, Metin (2011-01-01)
The reactions of some 1,3-dicarbonyl compounds with cycloheptatriene derivatives in the presence of Mn(OAc)(3) were examined. Cycloheptatriene forms mainly [2+3] and [6+3] dihydrofuran addition products derived from cycloheptatriene. However, the reaction of acetylacetone with cycloheptatriene substituted with an electron withdrawing group exclusively gave products derived from the norcaradiene structure. The formation mechanism of the products as well as the role of the substituent attached to cycloheptatr...
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Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the pr...
Synthesis of a bipyridine-derived achiral thiourea trifluoromethanesulfonic acid salt and its application as an additive in organocatalytic asymmetric reactions
Demir, Ayhan Sıtkı; BAŞÇEKEN, SİNAN (2013-10-16)
The host-guest complex of a proline-thiourea bipyridine trifluoromethanesulfonic acid salt can catalyze organocatalytic asymmetric reactions such as aldol, Michael, and Mannich in polar protic medium with high stereoselectivities. The privileged bipyridine backbone and the thiourea motif are essential to the activity and enantioselectivity through hydrogen bonding interactions.
Synthesis of ferrocene substituted pyrrolidine derivatives via Et2Zn catalyzed 1 3 dipolar cycloaddition reactions of azomethine ylides
Doğan, Özdemir (2001-05-01)
Synthesis of ferrocene substituted pyrrolidine derivatives via diethylzinc catalyzed 1,3-dipolar cycloadditions of azomethine ylides is described. Azomethine ylides were generated from glycine methyl ester and ferrocenecarboxaldehyde by the 'imine tautomerization' method and trapped with dipolarophiles to give the corresponding cycloadducts in reasonable yields and high regio- and stereoselectivity.
Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates
Polat-Cakir, Sidika; BEKSULTANOVA, Nurzhan; Doğan, Özdemir (Informa UK Limited, 2018-12-02)
A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.
Citation Formats
İ. Sevim, “Reactions of diethylaluminum cyanide with acyl phosphonates,” M.S. - Master of Science, Middle East Technical University, 2010.