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

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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

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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.