School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China.
Org Biomol Chem. 2014 Dec 21;12(47):9539-46. doi: 10.1039/c4ob01741b. Epub 2014 Oct 20.
The first catalytic asymmetric Povarov reaction of isatin-derived 2-azadienes with 3-vinylindoles was established in the presence of chiral phosphoric acid, which tolerates a wide range of substrates with generally excellent diastereoselectivity and good enantioselectivity (up to >95 : 5 dr, 89 : 11 er). This approach will greatly enrich the chemistry of the catalytic asymmetric Povarov reaction, in particular ketone-involved transformations. Furthermore, this protocol represents the first diastereo- and enantio-selective construction of a spiro[indolin-3,2'-quinoline] framework bearing an indole moiety. This novel type of spiro-compound not only contains two chiral centers, including one quaternary stereogenic center, but also integrates two biologically important structures of spiro[indolin-3,2'-quinoline] and indole, which may find medicinal applications after bioassay.
在手性磷酸的存在下，建立了色胺衍生的 2-氮杂二烯与 3-乙烯基吲哚的首例催化不对称 Povarov 反应，该反应对具有广泛底物的耐受性，具有一般优异的非对映选择性和良好的对映选择性（高达＞95：5 dr，89：11 er）。该方法将极大地丰富催化不对称 Povarov 反应的化学，特别是涉及酮的转化。此外，该方案代表了首例具有吲哚部分的螺[吲哚啉-3,2'-喹啉]骨架的非对映选择性和对映选择性构建。这种新型螺化合物不仅含有两个手性中心，包括一个季碳立体中心，而且还整合了螺[吲哚啉-3,2'-喹啉]和吲哚这两个重要的生物结构，经过生物测定后可能会有药用价值。
