Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in thepresence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution wasestablished. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate esterderivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR andconfirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of thepyrrole, 2c,e showed no diastereoselectivity.
|Journal||Iranian Journal of Chemistry and Chemical Engineering|
|Publication status||Published - 2008|
Maghsoodlou, M. T., Faramarz, R. C., Sayed Mostafa, H. K., Maryam, K., & Makha, M. (2008). Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution. Iranian Journal of Chemistry and Chemical Engineering, 27(1), 105-113. http://www.ijcce.ac.ir/