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

2008-11-21
Demir, Ayhan Sıtkı
Emrullahoglu, Mustafa
Pirkin, Eser
Akca, Nazmiye
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.

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, vol. 73, no. 22, pp. 8992–8997, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/62950.