Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, ROC.
J Am Chem Soc. 2010 Sep 15;132(36):12565-7. doi: 10.1021/ja106493h.
We report a highly stereoselective Au-catalyzed synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes. Formation of these highly strained anti-Bredt oxacycles implies the workability of an unprecedented 1,4-dipole of s-trans-methylene(vinyl)oxonium. This work reveals the feasibility of a formal [4 + 2] cycloaddition on an s-trans-heterodiene framework.
我们报告了一种高立体选择性的金催化合成 9-氧杂双环[3.3.1]壬-4,7-二烯的方法，该方法可由多种 1-氧代-4-氧基-5-炔烃得到。这些高度应变的反-Bredt 氧杂环的形成意味着前所未有的 s-顺式亚甲基（乙烯基）氧翁 1,4-偶极子的可操作性。这项工作揭示了在 s-顺式杂二烯骨架上进行形式[4 + 2]环加成的可行性。
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