Diastereoselective 1, 6-Asymmetric Induction to Obtain Chiral 4-Hydroxyethylaminobutanones by Using Methyltitanium Triisopropoxide

Hiroshi TAKAHASHI; Kazuo HATTORI; Kimio HIGASHIYAMA; Yumiko UENO

doi:10.1248/cpb.38.1062

Hiroshi TAKAHASHI, Kazuo HATTORI, Kimio HIGASHIYAMA, Yumiko UENO

Author information

Keywords: methyltitanium triisopropoxide, 1, 6-asymmetric induction, diastereoselective reaction, chiral 2-hydroxyethylamine, 1-phenylbitanone, chiral 2-phenyl-2-pentanol, (S)-4-isopropyl-1, 3-oxazolidine, (S)-prolinol, (S)-N-methylvalinol, (S)-4-phenyl-γ-valerolactone

JOURNAL FREE ACCESS

1990 Volume 38 Issue 4 Pages 1062-1065

DOI https://doi.org/10.1248/cpb.38.1062

Details

Abstract

The reactions of (S)-4-amino-1-phenylbutanones (3a-e) with methyllithium, methylmagnesium bromide, and methyltitanium triisopropoxide were studied. The reaction of the (S)-4-hydroxyethylamino derivatives (3a and 3d) with methyltitanium triisopropoxide gave 4a and 4d by 1, 6-asymmetric induction with diastereoselectivities of 78 and 70%.

Corresponding author

Register with J-STAGE for free!