Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Org Lett. 2011 Apr 1;13(7):1828-31. doi: 10.1021/ol2003447. Epub 2011 Mar 8.
The intramolecular carbosilylation of N-[2-(1,3-butenyl)aryl]carbamoyl chloride has been investigated. The reaction with hexamethyldisilane proceeds smoothly in the presence of a catalytic amount of Pd(η(3)-allyl)Cl to give oxindoles with an allylsilane functional group in good yield. The subsequent subjection of the products to a Sakurai-type reaction provides more advanced tricyclic spirooxindoles by controlling the stereochemistry of three contiguous stereogenic centers.
我们研究了 N-[2-(1,3-丁烯基)芳基]碳酰胺氯的分子内碳硅烷基化反应。在Pd(η(3)-烯丙基)Cl的催化量存在下，该反应与六甲基二硅烷反应顺利进行，以良好的收率得到具有烯丙基硅烷官能团的氧化吲哚。随后，通过控制三个相邻立体中心的立体化学，将产物进行 Sakurai 型反应，得到更高级的三环螺氧化吲哚。
