Tetrahedron

Synthesis of N-sulfonyl aziridines through regioselective opening of epoxides under solid-liquid PTC conditions

D Albanese, D Landini, M Penso, S Petricci

Index: Albanese, Domenico; Landini, Dario; Penso, Michele; Petricci, Silvia Tetrahedron, 1999 , vol. 55, # 20 p. 6387 - 6394

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Citation Number: 17

Abstract

The ring opening of epoxides 1 with 4-toluenesulfonamide (6) under solid-liquid phase transfer catalysis (SL-PTC) conditions afforded regioselectively β-sulfonamidoalcohols 7 in high yields. These were further converted into N-sulfonylaziridines 9 after activation of the hydroxy leaving group followed by ring closing in the presence of potassium carbonate.