路易斯酸催化烯基酰胺与三甲基硅基氰化物的非对映选择性多米诺反应构建螺吲哚啉
Lewis Acid-Catalyzed Diastereoselective Domino Reaction of Ene-Ynamide with Trimethylsilyl Cyanide to Construct Spiroindolines.
作者信息
Yamaoka Yousuke, Yamasaki Daisuke, Kajiwara Daigo, Shinozaki Makiko, Yamada Ken-Ichi, Takasu Kiyosei
机构信息
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.
出版信息
Org Lett. 2022 Jun 24;24(24):4389-4393. doi: 10.1021/acs.orglett.2c01607. Epub 2022 Jun 10.
The Zn(OTf)-catalyzed domino reaction of enamide-ynamides in the presence of trimethylsilyl cyanide as an external nucleophile to construct spirocyclic indolines was developed. This domino reaction involved cyclization of enamide to ynamide to generate 4',5'-dihydrospiro[indoline-3,3'-pyrrol]-1'-ium followed by cyanide addition to produce spiroindolopyrrolidines with good diastereoselectivity.
开发了在三甲基硅基氰作为外部亲核试剂存在下，Zn(OTf)催化的烯酰胺-烯炔酰胺的多米诺反应，用于构建螺环吲哚啉。该多米诺反应包括烯酰胺环化生成烯炔酰胺，生成4',5'-二氢螺[吲哚啉-3,3'-吡咯]-1'-鎓，随后进行氰化加成，以良好的非对映选择性生成螺吲哚并吡咯烷。
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