Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates

Download

index.pdf

Date

2011-05-13

Author

Seven, Ozlem
Polat-Cakir, Sidika
Hossain, Md. Shakhawoat
Emrullahoglu, Mustafa
Demir, Ayhan Sıtkı

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

159
views

0
downloads

The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of alpha-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary alpha-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 degrees C gave the secondary alpha-hydroxy phosphonates, while at -100 degrees C they afford the tertiary alpha-hydroxy phosphonates.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/62983

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2011.03.036

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds Demir, Ayhan Sıtkı; Akhmedov, IM; Sesenoglu, O (Elsevier BV, 2002-12-02) 2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into beta-enamino, beta-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.
Coupling of cyclopropylcarbene-chromium complex with ferrocenyl alkynes: synthesis of 5-ferrocenyl-5-hydroxy-2-cyclopentenones and 4-ferrocenyl-4-cyclopentene-1,3-diones Zora, Metin; Bueyuekguengoer, Orhan (Elsevier BV, 2007-05-07) The coupling of ferrocenyl alkynes with cyclopropylcarbene-chromium complex leads to ferrocenyl-substituted 2-cyclopentenones with or without a hydroxy substituent, namely 4-cyclopentene-1,3-diones, 2-cyclobutenones, and alpha, beta-unsaturated aldehydes in varying amounts. The reaction initially produces a cyclopentadienone intermediate, then to the double bond of which, bearing a ferrocenyl group, addition of water occurs to afford hydroxy-substituted 2-cyclopentenones. In all the products, the hydroxy gr...
Synthesis of various camphor-based chiral pyridine derivatives Tanyeli, Cihangir; Isik, M (Elsevier BV, 2004-07-19) (+)-beta-Hydroxymethylenecamphor 1 and enamines 2a-e were transformed into chiral camphor-based pyridine derivatives 3a-e via a tandem condensation reaction in good yields.
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...
Reaction of ferrocenylcarbene complexes of Cr, Mo and W with alkynes: Synthesis of ferrocenylcyclobutenones, ferrocenylfurans and ferrocenylketoesters Zora, Metin (Elsevier BV, 2001-07-09) Ferrocenylcarbene complexes of Cr, Mo and W react with alkynes to produce cyclobutenones, furans and/or ketoesters. The reaction is quite sensitive to the substituents of the alkyne, regardless of the identity of the metal. Cyclobutenones are formed only in the reactions of diphenylacetylene, a rare occurrence for metal carbene complexes. Ketoesters are secondary reaction products and result From oxidation of furan derivatives during the course of the reaction and/or silica-gel chromatography.

Citation Formats

O. Seven, S. Polat-Cakir, M. S. Hossain, M. Emrullahoglu, and A. S. Demir, “Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary alpha-hydroxy phosphonates,” TETRAHEDRON, pp. 3464–3469, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62983.