Darzens Reaction of Acyl Phosphonates with alpha-Bromo Ketones: Selective Synthesis of cis- and trans-Epoxyphosphonates

Date

2008-11-21

Author

Demir, Ayhan Sıtkı
Emrullahoglu, Mustafa
Pirkin, Eser
Akca, Nazmiye

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Acyl phosphonates with alpha-halo ketones in the presence of bases at room temperature afford cis- and trans-epoxyphosphonates in good chemical yields and high selectivities using different bases. The diastereoselectivity of this reaction is easily controlled by changing the base. Changing the base from CS(2)CO(3) to DBU changed the diastereomeric ratio (trans/cis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete conversion to the corresponding cis isomer.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/62950

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo801818p

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, M. Emrullahoglu, E. Pirkin, and N. Akca, “Darzens Reaction of Acyl Phosphonates with alpha-Bromo Ketones: Selective Synthesis of cis- and trans-Epoxyphosphonates,” JOURNAL OF ORGANIC CHEMISTRY, pp. 8992–8997, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62950.