Preparation of alcohols and 1,2-diols from epoxides and 1,3-dienes
作者:Mathew S. Sell、Heping Xiong、Reuben D. Rieke
DOI:10.1016/s0040-4039(00)61714-8
日期:1993.9
Formation of both alcohols and 1,2-diols containing a quaternary carbon center can be achieved in high yields in a one-pot synthesis utilizing active magnesium, epoxides, and 1,3-dienes.
Direct Synthesis of Spiro .delta.-lactones, Spiro-.gamma.-Lactones, and Alcohols from Substituted (2-Butene-1,4-diyl)magnesium Complexes
作者:Reuben D. Rieke、Matthew S. Sell、Heping Xiong
DOI:10.1021/jo00121a036
日期:1995.8
A convenient, one-pot process for the synthesis of spiro delta- and gamma-lactones and alcohols from conjugated dienes mediated by Rieke magnesium is described. This technique involves the treatment of a substituted (2-butene-1,4-diyl)magnesium complex with an epoxide or ketone at -78 degrees C, followed by the addition of carbon dioxide at 0 degrees C to room temperature. After acidic hydrolysis and subsequent warming, a spiro delta- or gamma-lactone accommodating both a quaternary carbon center and vinyl moiety at the beta-position is afforded in good isolated yield. Alternatively, acidic hydrolysis of the initially formed adduct at 0 degrees C furnishes an alcohol containing a quaternary carbon center in good to excellent chemical yield.