通过分子间氧杂迈克尔/迈克尔逐步环化反应合成四氢吡喃

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2024-07-25 DOI:10.1016/j.tetlet.2024.155215

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引用次数: 0

摘要

利用从 Baylis-Hillman 反应中获得的烯丙基醇和 2-(4-硝基苯基)丙烯酸甲酯，开发了一种分子间高非对映选择性氧杂迈克尔/迈克尔型逐步环化反应来合成四氢吡喃。以 DBU 为碱基，在 70 ℃ 条件下，这些分子的产率从低到高不等。这种方法为获得带有三个立体中心的四氢吡喃提供了一种方便且原子经济的方法，从而扩大了氧杂迈克尔反应的合成适用性和多功能性。

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Synthesis of tetrahydropyrans via an intermolecular oxa-michael/michael stepwise cycloaddition

An intermolecular highly diastereoselective oxa-Michael/Michael type stepwise cycloaddition was developed to synthesize tetrahydropyrans, using an allylic alcohol obtained from Baylis-Hillman reaction and methyl 2-(4-nitrophenyl) acrylate. These molecules were obtained in low to good yields using DBU as a base at 70 °C. This methodology provides a convenient and atom-economical approach for accessing tetrahydropyrans bearing three stereogenic centers, expanding the synthetic applicability and versatility of the oxa-Michael reactions.

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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.