C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Org Lett. 2012 Mar 2;14(5):1334-7. doi: 10.1021/ol300227a. Epub 2012 Feb 22.
The Schmittel cyclization was achieved at room temperature through triazole-gold (TA-Au) catalyzed propargyl vinyl ether rearrangement. Other tested L-Au catalysts gave complex reaction mixtures under identical conditions with no desired products observed. Importantly, because of the employment of mild conditions, sterically hindered groups (such as t-Bu) on allene termini were no longer required, which allowed successful synthesis of previously challenging substrates.
Schmittel 环化反应在室温下通过三唑金(TA-Au)催化的炔丙基乙烯基醚重排来实现。在相同条件下,其他测试的 L-Au 催化剂得到了复杂的反应混合物,没有观察到所需的产物。重要的是,由于采用了温和的条件,烯丙基末端的空间位阻基团(如 t-Bu)不再需要,这使得以前具有挑战性的底物能够成功合成。