Tetrahedron

Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1h-aziridine-2-car☐ ylate

…, AWM Adriaan, PW Mariëlle, J Legters, B Zwanenburg

Index: Thijs, Lambertus; Orskamp Jos; Adriaan; Marielle; Eenstra, Rolf W.; Legters, Johan; Zwanenburg, Binne Tetrahedron, 1990 , vol. 46, # 7 p. 2611 - 2622

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Citation Number: 38

Abstract

Sodium-E3-phenylglycidate (±)-2E was prepared using the Darzens' procedure. Classical resolution with 1-phenylethylamine afforded optically pure salts (+)-(2S, 3R)-2E and (-)-(2R, 3S)-2E. Alternatively,(±)-2E was converted into (±)-2Z by ring opening of ethyl ester (±) 1E with hydrogen bromide, followed by recyclization and saponification. Classical resolution of (±)-2Z with ephedrine afforded optically pure salts (+)-(2S, 3S)-2Z and (-)-(2R, 3R)-2Z ...