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Synthesis 2011(17): 2817-2821  
DOI: 10.1055/s-0030-1260153
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Marcos Hernández-Rodríguez*, Tania Castillo-Hernández, Karla Elisa Trejo-Huizar
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Del. Coyoacán, C. P. 04510, México, D.F., Mexico
Fax: +52(55)56224402; e-Mail: marcoshr@unam.mx;
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Publication History

Received 21 April 2011
Publication Date:
08 August 2011 (online)

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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

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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)].