Journal of the American Chemical Society

Highly regio-and stereoselective halohydroxylation reaction of 1, 2-allenyl phenyl sulfoxides. Reaction scope, mechanism, and the corresponding Pd-or Ni-catalyzed …

S Ma, H Ren, Q Wei

Index: Ma, Shengming; Ren, Hongjun; Wei, Qi Journal of the American Chemical Society, 2003 , vol. 125, # 16 p. 4817 - 4830

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Citation Number: 85

Abstract

A highly regio-and stereoselective halohydroxylation of 1, 2-allenyl sulfoxides with X+ and water was developed. The reaction shows E-stereoselectivity. In the iodohydroxylation reaction, I2 was used to introduce the iodine atom. For bromohalohydroxylation, CuBr2, NBS, or Br2 can be used. When using I2, NBS, or Br2, the addition of LiOAc⊙ 2H2O is necessary for high yields of the halohydroxylation products. The chlorohydroxylation ...