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Asymmetric reduction of various ketones with the sodium salts of .ALPHA.-amino acid borane complexes.

1979; Pharmaceutical Society of Japan; Volume: 27; Issue: 6 Linguagem: Inglês

10.1248/cpb.27.1479

1347-5223

N. UMINO, T. IWAKUMA, Nobuo Itoh,

Chemical Synthesis and Analysis

The sodium salts of amino acid borane complexes (1) produced from equimolar amount of NaBH4 and optically active α-amino acids in tetrahydrofuran at room temperature reduced various ketones to the corresponding optically active alcohols (2-62% optical yield). Sodium prolinate borane complex (2) gave the best results. Asymmetric reduction of (3) with sodium L-prolinate borane complex (2) followed by catalytic hydrogenolysis of benzyl and carbobenzoxy groups gave (4), a cardiotonic agent, in 62% optical yield.