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Michael additions of [(diphenylmethylene)amino]acetonitrile (1) to α,β-unsaturated ketones (chalkones) (2) under aqueous conditions allow for the highly diastereoselective synthesis of substituted 2-amino-5-oxonitriles (3). Selective removal of diphenylmethylene protecting group, followed by in situ cyclization, gives 3,5-diaryl-3,4-dihydro-2H-pyrrole-2-carbonitriles (4). [ABSTRACT FROM AUTHOR]

New dimethylphosphinyl-substituted tetrahydropyrroles 3, 5, 6 and 8 have been synthesized via 1,3-cycloaddition reaction of the N-(4-chlorophenylmethylene)aminomethyl-dimethylphosphinoxide (1) to benzylideneacetophenone, ethyl cinnamate and cinnamonitrile. The structure of the compounds was confirmed by elemental analysis, IR, 1 H-, and 31 P 1 H-NMR spectroscopy and in some cases by mass spectrometry, as well. [ABSTRACT FROM AUTHOR]