Highly Diastereoselective 1, 5-Asymmetric Induction to 3-Oxazolidino-1-phenylpropan-1-ones by Using Organotitanium Triisopropoxides

Abstract

The reaction of (S)-3-4'-isopropyl-1'-3'-oxazolidino-1-phenylpropan-1-ones (1a, 1b) with 4 mol eq of various organotitanium triisopropoxides in ether at room temperature for 18-20 h gave 1-alkyl(or aryl)-3-N-alkyl(or arymethyl)-N-1'-isopropyl-2'-hydroxyethylamino-1-phenyl-propan-1-ols (2a-h) in good yields.This 1, 5-asymmetric induction proceeded with extremely high diastereoselectivity. The absolute configurations of 2d and 3d were determined by X-ray analysis.