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)
The hexenitol (III) mentioned in the title is alkylated with the organometallic compounds (IV) to form the 1‐substituted glucals (V), (VI), and/or the 3‐substituted regioisomers (VII).
Das aus dem Salz (I) freigesetzte Titelphosphoran (II) reagiert in situ mit CS2 zu den Verbindungen (III), (IV) und (vermutlich) (V) und nicht zu dem erwarteten Thioketen (VI) oder seinem für organische Reaktionen wichtigen Dimeren (VII).
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