Highly selective intermolecular one-pot three component 1,3-dipolar cycloaddition reaction of aldehydes, with phosphonates and proline

Date

2017-07-27

Author

Subasi, N. Tuna
Yalcinkaya, Hatice
Demir, Ayhan Gürbüz

Metadata

Show full item record

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

Item Usage Stats

95
views

0
downloads

The use of L-proline to act as an organocatalyst in the aldol reaction of acylphosphonates and non enolizable aldehydes failed; however, it reacted with the aldehydes to afford azomethine ylides after decarboxylation that in turn underwent 1,3-dipolar cycloaddition with the acylphosphonates to form a bicyclic hexahydropyrrolo[1,2-c]oxazol-1-ylphosphonates in good yield. No azomethine ylide formation was observed on the reaction of acylphosphonates with proline.

Subject Keywords

Dipolar cycloaddition, Azomethine ylide, Acylphosphonate, Proline

URI

https://hdl.handle.net/11511/62734

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/j.tet.2017.05.091

Collections

Department of Educational Sciences, Article

Suggestions

OpenMETU
Core

Enantioselective synthesis of furyl-substituted pyrrolidines Araz, Mihrimah; Doğan, Özdemir; Department of Chemistry (2019) Asymmetric 1,3-Dipolar Cycloaddition (DC) reactions of azomethine ylides are important for the synthesis of pyrrolidines. These reactions may give enantiomerically pure compounds in the presence of a chiral catalyst in a single step. Therefore, many groups have studied this reaction to synthesize aryl-substituted pyrrolidines in enantiomerically rich form. Although the aryl-substituted pyrrolidine synthesis is very common, the studies involving the heteroaryl-substituted pyrrolidines are quite rare. In gene...
Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex Erturk, Erkan; Demir, Ayhan Sıtkı (Elsevier BV, 2008-08-04) The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph(3)P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed.
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.
Homoconjugated and Spiro Push-Pull Systems: Cycloadditions of Naphtho- and Anthradiquinones with Electron-Rich Alkynes Dengiz, Çağatay (2017-07-01) We report the synthesis and characterization of three new classes of push-pull chromophores using [2+2]-cycloaddition reactions of electron-rich alkynes and electron-poor alkenes. Previous investigations have focused on the reactions of cyano-substituted electron acceptors. This study demonstrates that cyano-free electron acceptors, naphtho- and anthradiquinones, can also be used to access extended push-pull systems. The effects of the structural changes on the spectroscopic and electronic properties were i...
Asymmetric organocatalytic direct Mannich reaction of acetylacetone and isatin derived ketimines: Low catalyst loading in chiral cinchona-squaramides İŞİBOL, Duygu; Karahan, SEDA; Tanyeli, Cihangir (2018-02-07) A highly enantioselective synthesis of 3-amino-2-oxindoles by direct Mannich reaction between acetylacetone and N-carbamoyl isatin ketimine has been described herein. Corresponding chiral adducts were obtained in high yields (up to 98%) and with excellent enantioselectivities (up to >99% ee) by very low (1 mol%) catalyst loading of 2-adamantyl substituted bifunctional cinchona-squaramide.

Citation Formats

N. T. Subasi, H. Yalcinkaya, and A. G. Demir, “Highly selective intermolecular one-pot three component 1,3-dipolar cycloaddition reaction of aldehydes, with phosphonates and proline,” TETRAHEDRON, pp. 4329–4334, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62734.