Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution
Abstract: Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in the presence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution was established. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate ester derivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR and confirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of the pyrrole, 2c,e showed no diastereoselectivity
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