Stereoselective preparation of 3-alkanoylprop-2-en-1-ol derivatives

M Sada, S Ueno, K Asano, K Nomura, S Matsubara

Index: Sada, Mutsumi; Ueno, Shizue; Asano, Keisuke; Nomura, Kenichi; Matsubara, Seijiro Synlett, 2009 , # 5 p. 724 - 726

Full Text: HTML

Citation Number: 8

Abstract

As shown in Table [¹] , 2-(oxiran-2-yl)-1-phenylethanone (2a, R = Ph) was treated with various amines (entries 1-5). Among them, triethylamine and N,N-dimethylpyridin-4-amine (DMAP) gave the satisfactory results. In both cases, the corresponding E-isomer was obtained exclusively. Treatment of 2a with pyridine, imidazole, or Hünig's base (i-Pr 2 NEt) was suffered from low conversion. A use of catalytic amount of DMAP with a stoichiometric amount of pyridine or ...