Department of Chemistry, 232 Choppin Hall, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Org Lett. 2016 Jun 17;18(12):3002-5. doi: 10.1021/acs.orglett.6b01376. Epub 2016 Jun 6.
We report a new strategy toward the synthesis of highly functionalized carbazoles via 2-(silyloxy)pentadienyl cation intermediates, which were generated upon ionization of vinyl-substituted α-hydroxy silyl enol ethers under Brønsted acid catalysis. These electrophilic species were found to readily undergo cascade reactions with substituted indoles to generate carbazole molecular scaffolds in good yields via a sequence of regioselective nucleophilic addition, followed by intramolecular dehydrative cyclization.
我们报告了一种通过 2-（硅氧基）戊二烯基阳离子中间体合成高度官能化咔唑的新策略，该中间体是在 Brønsted 酸催化下，通过乙烯基取代的α-羟基硅基烯醇醚的离解生成的。这些亲电物种被发现能够与取代的吲哚发生级联反应，通过区域选择性亲核加成，然后进行分子内脱水环化，以良好的收率生成咔唑分子骨架。
