Abstract
Abstract A new series of dialkyl(pyrrolidin-2-yl)phosphonates was synthesized by regiospecific intramolecular aminomercuration of α-amino alkenylphosphonates followed by sodium borohydride reduction. The formation of dialkyl (2,5-dialkyl pyrrolidin-2-yl) and dialkyl (5-alkyl pyrrolidin-2-yl)phosphonates was stereoselective and the stereochemistry of diastereomers was assigned using X-ray analysis and 1H, 13C and 31P-NMR data. EPR evidence for the production of free radicals during the borohydride reduction of the intermediate organomercurials was achieved by spin-trapping experiments.
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