Abstract
The synthesis of all four possible stereoisomers of enantiopure and diastereomerically pure or highly enriched α-branched [2.2]paracyclophanylalkylamines is described. Key step is the nucleophilic 1,2-addition of alkyllithium reagents to hydrazones of 4-formyl[2.2]paracyclophane derived from the chiral auxiliaries SAMP/RAMP and RAMBO/SAMBO via chromatographic epimer separation. Reductive N-N bond cleavage of the resulting hydrazines, followed by treatment with benzyloxycarbonyl chloride afforded the N -Cbz-protected diastereo- and enantiopure (de, ee ÷ 99%) or diastereomerically enriched (de = 89-96%) title amines.
Key words
amines - cyclophanes - hydrazones - nucleophilic addition - planar chirality
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