Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates

2009-05-18
Demir, Ayhan Sıtkı
Aybey, Asuman
Emrullahoglu, Mustafa
Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl cyanophosphonate to the cyanohydrin phosphate anion.
SYNTHESIS-STUTTGART

Suggestions

Benzaldehyde Lyase-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
Ayhan, Peruze; Demir, Ayhan Sıtkı (Wiley, 2011-03-07)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.
Metal triflates-catalyzed conjugate addition of homochiral Pyrroles to alpha,beta-unsaturated esters
Unaleroglu, C; Temelli, B; Demir, Ayhan Sıtkı (Georg Thieme Verlag KG, 2004-10-18)
The Friedel-Crafts reaction of homochiral pyrrole derivatives with alpha,beta-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectively at C-5 of pyrrole. The diastereoisomers were separated by column chromatography.
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.
Chemoenzymatic synthesis of both enantiomers of 2-chloro-1-(2-furyl)ethanol
Gercek, Z; Karakaya, D; Demir, Ayhan Sıtkı (Elsevier BV, 2005-05-23)
Enzyme catalyzed transesterification of rac-2-chloro-1-(2-furyl)ethanol rac-1 using vinyl acetate afforded the enantiomers of 2-chloro-1-(2-furyl)ethanol 1 and 2-chloro-1-(2-furyl)ethyl acetate 2 in high enantiomeric excess. Several lipases were used for the kinetic resolution of racemic 2-chloro-1-(2-furyl)ethanol l, in which the lipases from Pseudomonas cepacia, Candida antarctica and Candida cylindracea displayed high enantioselectivity towards 1.
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...
Citation Formats
A. S. Demir, A. Aybey, and M. Emrullahoglu, “Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates,” SYNTHESIS-STUTTGART, pp. 1655–1658, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62854.