Asymmetric induction in the Neber rearrangement of simple ketoxime sulfonates under phase-transfer conditions: experimental evidence for the participation of an …

…, M Takahashi, K Doda, K Maruoka

Index: Ooi, Takashi; Takahashi, Makoto; Doda, Kanae; Maruoka, Keiji Journal of the American Chemical Society, 2002 , vol. 124, # 26 p. 7640 - 7641

Full Text: HTML

Citation Number: 92

Abstract

Phase-transfer catalysis has been successfully utilized for the Neber rearrangement of simple ketoxime sulfonates. For instance, treatment of (Z)-1a with p-toluenesulfonyl chloride (1.2 equiv), tetrabutylammonium bromide (5 mol%) and MeOH (10 equiv) in toluene-50% KOH aqueous solution (volume ratio= 3: 1) at 0° C for 2 h, and subsequent benzoylation followed by acidic hydrolysis afforded the protected α-amino ketone 2a in 80% isolated ...