Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations

Date

2007-09-14

Author

Demir, Ayhan Sıtkı
Reis, Barbaros
Reis, Omer
Eymuer, Serkan
Goellue, Mehmet
Tural, Servet
Saglam, Gueluezar

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Organic Chemistry

URI

https://hdl.handle.net/11511/57343

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo0710073

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Department of Chemistry, Article

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Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates Demir, Ayhan Sıtkı; Aybey, Asuman; Emrullahoglu, Mustafa (Georg Thieme Verlag KG, 2009-05-18) 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.
Alkylation of l- and d-menthyl pentanoate with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane Demir, Ayhan Sıtkı (Informa UK Limited, 1996-01-01) The alkylation of l- and d-menthyl valerate with n-hexyl iodide and with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane gave modest levels of diastereoselection. The chirality of the ester group favoured slight degree of selectivity. The chiral centers had limited impact on diastereoselectivity.
Oxidative ring opening reactions of a-hydroxy ketones Aybey, Ayşe; Demir, Ayhan Sıtkı; Department of Chemistry (2008) Chiral polyfunctionalized 1,5-dicarbonyl compounds are important synthetic intermediates and starting materials for many biologically active compounds so their synthesis has a great importance in the literature. In the first step, 1,3-cyclohexandione and other b-diketone derivatives are protected under acid catalyzation and their corresponding b-keto enol ether derivatives are obtained. These b-keto enol ethers are then converted to a-acetoxy enones in racemic form by Mn(OAc)3 mediated oxidation. Enzymatic ...
Synthesis of chiral lactones via the baeyer villiger oxidation of cyclic aromatic acetoxy ketones novel annulation reactions of 2-propynyl-1,3-dicarbonyl compounds to form pyrroles addition of acyl phosphonates to diethyl cyanophosphonate (depc) Aybey, Asuman; Demir, Ayhan Sıtkı; Department of Chemistry (2009) Chiral Baeyer-Villiger (BV) oxidation of cyclic ketones allows rapid access to asymmetric lactones as valuable intermediates in organic chemistry and frequently encountered precursors in enantioselective synthesis. In the first part, BV oxidation of functionalized ketones, especially cyclic -hydroxy and acetoxy ketones is described which could be a straightforward route to the -hydroxy lactones and -hydroxyalkanoic acid derivatives. The -acetoxylation of indanone, tetralone and chromanone derivatives by usi...
Transition structures, energetics, and nucleus-independent chemical shifts for 6 pi electrocyclizations of dienylketenes to cyclohexadienones: A DFT study Zora, Metin (American Chemical Society (ACS), 2004-03-19) 6pi electrocyclizations of dienylketenes to 2,4-cyclohexadienones have been investigated at the (U)B3LYP/6-31G* level and found to be a favored and exothermic process for most dienylketenes. As evidenced by calculations, dienylketene cyclizations proceed via a pseudopericyclic process. If the terminal double bond of dienylketenes is embedded into a benzenoid-type aryl moiety, the partial or complete loss of aromaticity, as indicated by NICS values, increases the activation barrier and makes the reaction les...

Citation Formats

A. S. Demir et al., “Cyanide ion promoted addition of acyl phosphonates to ethyl cyanoformate: Synthesis of tertiary carbinols via tandem carbon-carbon bond formations,” JOURNAL OF ORGANIC CHEMISTRY, pp. 7439–7442, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57343.