Synthesis of β-hydroxy sulfones via opening of hydrophilic epoxides with zinc sulfinates in aqueous media
作者:Nataliya Chumachenko、Paul Sampson
DOI:10.1016/j.tet.2006.02.043
日期:2006.5
Reaction of hydrophilic epoxides (ethylene oxide and propylene oxide) with readily accessible zinc sulfinates in aqueous solution under essentially neutral conditions afforded beta-hydroxy sulfones in good yields. This method avoids the need for organic solvents and produces ZnO as the only major reaction byproduct. 2-(Methylsulfonyl)ethanol, a common reagent for the protection of various functional groups, was obtained by this methodology from ethylene oxide in 78% yield. Reaction of various simple zinc alkane- and benzenesulfinates with propylene oxide proceeded regioselectively in 63-67% yield. The corresponding opening of these epoxides with zinc 1,3-butadiene-1-sulfinate afforded 1-butadienyl beta-hydroxyalkyl sulfones in 30% yield. Mechanistic studies revealed that the yields of these products were limited by their consumption in competing intra- and intermolecular Michael addition processes. (c) 2006 Elsevier Ltd. All rights reserved.
ALCUDIA, F.;BRUNET, E.;GARCIA, RUANO, J. L.;RODRIGUEZ, J. H.;SANCHEZ, F., J. CHEM. RES. MICROFICHE, 1982, N 10, 284-285
作者:ALCUDIA, F.、BRUNET, E.、GARCIA, RUANO, J. L.、RODRIGUEZ, J. H.、SANCHEZ, F.
DOI:——
日期:——
Alcudia Gonzalez, F.; Brunet Romero, E.; Garcia Ruano, J. L., Journal of Chemical Research, Miniprint, 1982, # 10, p. 2826 - 2850
作者:Alcudia Gonzalez, F.、Brunet Romero, E.、Garcia Ruano, J. L.、Rodriguez Ramos, J. H.、Sanchez Alonso, F.