杂环邻喹啉二甲烷与2-芳基烷-1,3-茚二酮经三胺中间体合成四氢螺咔唑-茚二酮的不对称Diels-Alder反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-01-30 DOI:10.1016/j.tetlet.2024.155428

Raghupathi Mutyala , K. Rajitha , Jagadeesh Babu Nanubolu , Rajesh Chandra

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引用次数: 0

摘要

以吲哚丙烯醛为原料，在脯氨醇衍生催化剂的存在下，原位生成杂环喹诺二甲烷与芳啶-1,3-茚二酮进行了对映选择性Diels-Alder反应。该反应通过三胺途径进行，产生手性四氢螺卡唑-吲哚-1,3-二酮。该反应具有高至优异的对映选择性和非对映选择性，收率优异。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Asymmetric Diels–Alder reaction of heterocyclic o-quinodimethane with 2-arylidene-1,3-indanedoines to access tetrahydrospirocarbazole-indanediones via trienamine intermediate

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Asymmetric Diels–Alder reaction of heterocyclic o-quinodimethane with 2-arylidene-1,3-indanedoines to access tetrahydrospirocarbazole-indanediones via trienamine intermediate

Enantioselective Diels–Alder reaction of in situ generated heterocyclic quinodimethane from indolylacrylaldehyde with arylidine-1,3-indanedinones is carried out in the presence of chiral prolinol-derived catalysts. The reaction proceeds through a trienamine pathway, resulting in chiral tetrahydrospirocarbazoles-indane-1,3-diones. The reaction proceeds with high to excellent enantio- and diasteroselectivities with excellent yields.

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.