Institut für Chemie der Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany.
J Org Chem. 2010 Dec 3;75(23):8315-8. doi: 10.1021/jo1018443. Epub 2010 Nov 9.
The Me(3)SiOTf-mediated condensation of 1-ethoxy-2-fluoro-1,3-bis(trimethylsilyloxy) 1,3-dienes with 3-cyanochromones afforded 3-cyano-2-(4-ethoxy-3-fluoro-2,4-dioxobutyl)chroman-4-ones. Their reaction with triethylamine afforded fluorinated azaxanthones or biaryls. The product distribution depends on the structure of the diene. The formation of the biaryls can be explained by an unprecedented domino "retro-Michael/aldol/fragmentation" reaction.
Me(3)SiOTf 介导的 1-乙氧基-2-氟-1,3-双(三甲基甲硅氧基)1,3-二烯与 3-氰基色酮的缩合反应得到 3-氰基-2-(4-乙氧基-3-氟-2,4-二氧代丁基)色满-4-酮。它们与三乙胺的反应生成氟化氮杂蒽酮或联芳烃。产物的分布取决于二烯的结构。联芳烃的形成可以通过前所未有的串联“逆迈克尔/羟醛/断裂”反应来解释。
