Reaction of peroxyacetals with silyl ketene acetals: synthesis of 3-peroxyalkanoates and 3-peroxyalkanals
作者:P.H Dussault、R.J Lee、J.A Schultz、Y.S Suh
DOI:10.1016/s0040-4039(00)00914-x
日期:2000.7
Lewis acid-mediated reaction of monoperoxyacetals with silyl ketene acetals (SKAs) provides an efficient approach to 3-peroxyalkanoates. Propionate SKAs react with aliphatic peroxyacetals to furnish 3-peroxy-2-methyl alkanoates with modest anti-selectivity. Although acetate and thioacetate SKAs are less reactive, the latter react with unsaturated peroxyacetals to furnish peroxyalkenoates and -alkadienoates
路易斯酸介导的单过氧缩醛与甲硅烷基烯酮缩醛(SKA)的反应为3-过氧链烷酸酯提供了一种有效的方法。丙酸酯SKA与脂族过氧缩醛反应,以适度的反选择性提供3-过氧-2-甲基链烷酸酯。尽管乙酸盐和硫代乙酸盐SKA的反应性较低,但后者与不饱和过氧乙缩醛反应以提供过氧链烯酸酯和-链二烯酸酯,它们经过化学选择性还原成3-过氧烯醛和3-过氧链烯醛。