Publication Details (including relevant citation information):
Ayhan S. Demir, Mustafa Emrullahoglu, Eser Prikin, Nazmiye Akca, J. Org. Chem.,2008, 73 (22), pp 8992–8997, DOI:10.1021/jo801818p
Acyl phosphonates with α-halo ketones in the presence of bases at room temperature affordcis- 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 Cs2CO3 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.
Address (URL): http://pubs.acs.org/doi/abs/10.1021/jo801818p