Duan Ya-Nan, Cui Li-Qian, Zuo Lin-Hong, Zhang Chi
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China).
Chemistry. 2015 Sep 7;21(37):13052-7. doi: 10.1002/chem.201502450. Epub 2015 Jul 27.
We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative α,β'- bifunctionalization of β-ketoesters and β-diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
我们开发了一种方法，可在无金属条件下实现可回收的高价碘介导的β-酮酯和β-二酮的直接脱氢α,β'-双官能化，这为合成苯并稠合的2,3-二氢呋喃提供了一种直接的方法。这种高效、温和的方法具有广泛的底物范围和良好的官能团耐受性，用于天然存在的酚糖苷的保护苷元的多步合成。提出了一种涉及迈克尔加成到烯酮中间体并随后进行氧化环化的机理。
