ChemInform Abstract: (1′S,4S)‐2‐Aryl‐4‐(1′‐hydroxybenzyl)‐4,5‐dihydrooxazole as a Useful Chiral Auxiliary for the Synthesis of β‐Amino Acids and β‐Lactams in a Highly Stereoselective Manner.

Abstract

stereochemistry stereochemistry (general, optical resolution) O 0030 07 -038 (1'S,4S)-2-Aryl-4-(1'-hydroxybenzyl)-4,5-dihydrooxazole as a Useful Chiral Auxiliary for the Synthesis of β-Amino Acids and β-Lactams in a Highly Stereoselective Manner. -The addition reaction of lithium amide or the imine (V) to the substrates (I) or (IV) bearing a chiral auxiliary derived from (1S,2S)-2-amino-1-phenylpropane-1,3-diol generates β-amino acid esters (III) or β-lactams (VI) in moderate stereoselectivity. -(SHIMIZU, M.; MARUYAMA, S.; SUZUKI, Y.; FUJISAWA, T.; Heterocycles 45 (1997) 10, 1883-1889; Dep. Chem. Mater., Fac. Eng., Mie Univ., Tsu, Mie 514, Japan; EN)