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The regioselective Michael addition of the carbanion of 2-phenylacetonitrile (R2 = Ph) and malononitrile (R2 = CN) to fluoroalkylated α,β-unsaturated imines 1 is described. Fluorinated imines 1 were used as intermediates for the regioselective 1,4-addition and synthesis of functionalized fluorinated primary enamines 5 and 7, fluorine-containing trans-3,4-dihydro-2-aminopyridines 2, and fluorinated 2-aminopyridines 4 and 8, which were obtained with total atom economy. Derivatives 2 and 8 were also prepared by an intramolecular cyclocondensation reaction of functionalized fluorinated primary enamines 5 and 7, respectively, in the presence of a base (NaH). [ABSTRACT FROM AUTHOR]

A simple and efficient stereoselective synthesis of aziridine-2-phosphonate-3, and -phosphine oxide 5 by diastereoselective addition of Grignard reagents to 2H-azirine phosphonate 1 and -phosphine oxide 4 is reported. Similarly, the addition of heterocyclic amines and benzenethiol to aziridines 1 and 4 yielded functionalized aziridines 10, 11, and 18. These aziridines are used as intermediates for the regioselective synthesis of β-aminophosphine oxides 6 and α-aminophosphonates 7, as well as α-aminophosphonates 8. Phenylsulfenyl-substituted α-aminophosphorus derivatives 15 and 19 are obtained directly from benzenethiol and 2H-azirine phosphonates 1 and -phosphine oxides 4. [ABSTRACT FROM AUTHOR]