Men Wei-dong
2013
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Journal
Journal of Donghua University
Abstract
1,2,3,4-Tetrahydronaphthalen-1-amine and its derivative were a series of important synthetic intermediates for bioactive compounds. Acylation of optically pure (R)-and(S)-1, 2, 3, 4-tetrahydronaphthalen-1-amine with acetic anhydride, benzoyl chloride and phthalic anhydride followed by oxidation with potassium permanganate to give acylated aminonaphthyl ketones in yields of 65%~85%. These aminonaphthyl ketones were reduced stereoselectively by sodium borohydride(NaBH4) or diisobutylaluminium hydride(DIBAL-H) to afford the aminonaphthyl alcohols mainly in cis-form, which was confirmed by nuclear Overhauser effect(NOE) obtained by 2D1H NMR. When (R)-and(S)-phthalic protected aminonaphthyl ketone was reduced with DIBAL-H, cis-aminonaphthyl alcohols 4ca and 7ba were obtained as major product in diastereomeric excesses'(de) percentages of 92.6% and 98.2%, respectively.