Chemical and Pharmaceutical Bulletin
Asymmetric Reduction of Aromatic Ketones. I. Enantioselective Synthesis of Denopamine
Takayuki KAWAGUCHIKunio SAITOKenji MATSUKITakeo IWAKUMAMikio TAKEDA
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Volume 41 (1993) Issue 4 Pages 639-642

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Abstract

Asymmetric reduction of the N-protected amino ketone (2) with serveral chiral reducing agents, i.e., (R)-(+)-2-amino-3-methyl-1, 1-diphenylbutanol (6)-borane complex (method A), (S, S')-N, N'-dibenzoylcystine (7)-LiBH4-ROH complex (method B), and sodium (S)-prolinate-borane complex (8) (method C), was investigated in an attempt to synthesize denopamine (1) enantioselectively. Reduction of 2f by method B in tetrahydrofuran at 2-3°C gave the best result (88% ee with 95% chemical yield).

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