Stereoselective Reactions. XIX. Asymmetric Dihydroxylation of Olefins by Employing Osmium Tetroxide-Chiral Amine Complexes

Kiyoshi TOMIOKA; Yuichi SHINMI; Kunihiko SHIINA; Makoto NAKAJIMA; Kenji KOGA

doi:10.1248/cpb.38.2133

Kiyoshi TOMIOKA, Yuichi SHINMI, Kunihiko SHIINA, Makoto NAKAJIMA, Kenji KOGA

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Keywords: asymmetric synthesis, dihydroxylation, chiral ligand, diol, amino acid, pyridine, osmium tetroxide

JOURNAL FREE ACCESS

1990 Volume 38 Issue 8 Pages 2133-2135

DOI https://doi.org/10.1248/cpb.38.2133

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Abstract

Enantioselective dihydroxylation of E-stilbene afforded (1S, 2S)-1, 2-diphenyl-1, 2-ethanediol in 70% ee by employing a stoichiometric amount of osmium tetroxide-chiral amine 5, prepared from N-methylephedrine and 2-bromopyridine.

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