硝基酮与二氟丙烯酸酯[3 + 2]环加成法非对映选择性合成5,5-二氟异恶唑烷

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-05-08 DOI:10.1016/j.tetlet.2025.155647

Miaomiao Zhang , Lingyu Kong , Shengqiang Li, Shang Gao, Xuanyi Li

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引用次数: 0

摘要

将二氟乙烯（CF2）基团掺入到生物分子的主链中是一种很有吸引力的药物开发策略。本文描述了在无催化剂条件下，通过硝基酮和非对称四取代二氟丙烯酸酯之间的偶极[3 + 2]环加成合成5,5-二氟异恶唑烷的非对映选择性反应。该反应条件温和，产率中高，具有优异的区域选择性和非对映选择性。DFT计算表明，氮中心构型发生了自发反转。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Diastereoselective synthesis of 5,5-Difluoroisoxazolidine via [3 + 2] cycloaddition between Nitrones and Difluoroacrylates

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Diastereoselective synthesis of 5,5-Difluoroisoxazolidine via [3 + 2] cycloaddition between Nitrones and Difluoroacrylates

The incorporation of difluoromethylene (CF₂) group into the backbone of biomolecules is an appealing strategy in the drug development. We describe herein a diastereoselective synthesis of 5,5-difluoroisoxazolidine via dipolar [3 + 2] cycloaddition between nitrones and unsymmetric tetra-substituted difluoroacrylates under catalyst-free conditions. This reaction features mild conditions, moderate to good yield as well as excellent regio- and diastereo-selectivities. DFT calculations showed that a spontaneous inversion of the configuration of nitrogen center was involved.

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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.