Morris William J, Shair Matthew D
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Org Lett. 2009 Jan 1;11(1):9-12. doi: 10.1021/ol8022006.
Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-beta-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-beta-glycosides in high yield and high selectivity. The high beta-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control.
异头碳O-烷基化/芳基化反应被应用于2-脱氧-β-糖苷的合成。在二氧六环中用氢化钠处理内酯醇，随后加入亲电试剂，可高产率、高选择性地生成2-脱氧-β-糖苷。此处观察到的高β-选择性证明了在动力学控制下，缩醛立体选择性形成过程中存在强大的立体电子效应。
