Organocatalytic enantioselective (4+3) cyclization for the synthesis of spiro-fused heterocyclic compounds containing isoindolinone, oxepine and indole moieties,Chemical Communications

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Organocatalytic enantioselective (4+3) cyclization for the synthesis of spiro-fused heterocyclic compounds containing isoindolinone, oxepine and indole moieties
Chemical Communications ( IF 4.3 ) Pub Date : 2024-08-12 , DOI: 10.1039/d4cc03230f
Kanghua Rui ₁ , Shaoying Huang ₁ , Yinong Wu ₁ , Hanxiao Shen ₁ , Xufeng Lin ₁

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A refined strategy has been developed to control the regioselective asymmetric (4+3) cyclization of α-(3-isoindolinonyl) propargylic alcohols with 2-indolylmethanols, utilizing chiral phosphoric acid catalysis. This innovative organocatalytic cyclization yields spiro isoindolinone-oxepine-fused indoles featuring a spiro-quaternary stereocenter in high yields and enantioselectivities, facilitated by the solvent of 1,1-dichloro-1-fluoroethane and the additive of hexafluoroisopropanol. Additionally, the photophysical properties of product 3k are examined, revealing bright fluorescence both in the solution and the solid state.

中文翻译：

有机催化对映选择性 (4+3) 环化合成含有异吲哚酮、氧杂环庚烷和吲哚部分的螺稠杂环化合物

利用手性磷酸催化，开发了一种精细策略来控制 α-(3-异吲哚啉基) 炔丙醇与 2-吲哚甲醇的区域选择性不对称 (4+3) 环化。这种创新的有机催化环化反应在 1,1-二氯-1-氟乙烷溶剂和六氟异丙醇添加剂的促进下，以高产率和对映选择性产生具有螺环季立体中心的螺异吲哚酮-氧杂环戊烷稠合吲哚。此外，还检查了产品3k的光物理性质，显示出溶液和固态均发出明亮的荧光。

更新日期：2024-08-12

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