Asymmetric Synthesis of 1-(9-Anthracenyl)ethylamine and Its Trifluoro­methyl Analogue via Nucleophilic Addition to an N-(tert-Butylsulfinyl)imine

Abstract

Asymmetric synthesis of the 9-anthracenyl analogues of 1-phenylethylamine and 2,2,2-trifluoro-1-phenylethylamine was achieved via nucleophilic addition to the corresponding N-(tert-butylsulfinyl)imine.

Key words

amines - asymmetric synthesis - chiral auxiliaries - tert-butanesulfinamide - trifluoromethyl compounds

References

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8

Even with low selectivity the difference in R _f of the diastereomers is large enough for separation by regular flash chromatography [ΔR _f  = 0.23 (hexanes-EtOAc, 1:1)].