Synthesis of trans-2-(1-aryl-1-methylethyl)cyclohexylamines

[GRAPHICS] As a first example of opening a secondary aziridine with a tertiary carbanion, the title amines (3a-c, aryl = phenyl, 4-tert-butylphenyl, 2-naphthyl) were synthesized by opening N-(diphenylphosphinoyl)-7-azabicyclo[4.1.0]heptane, aziridine 1, with the corresponding alpha-potassium isopropylarenes, followed by hydrolysis of the resulting phosphinamides 2a-c.