糖醇促进烯基硼酸的非对映选择性光催化[2 + 2]二聚化反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-09-15 DOI:10.1016/j.tetlet.2025.155827

Anastasia Charlery, Shrey P. Desai, Matthew T. Zambri, Mark S. Taylor

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引用次数: 0

摘要

在糖醇中位赤藓糖醇的存在下，反式2-芳基乙烯基硼酸经过区域选择性和非对映选择性光催化[2 + 2]环加成，生成全反式取代的环丁烷-1,2-二（硼酸）衍生物。提出了一种共价模板机制，涉及原位形成2:1硼酸：四醇加合物-可能是混合硼酯/半硼酯。该方案已应用于各种取代的反式2-芳基乙烯基硼酸衍生物，提供了手性，c2对称的环丁烷衍生物，这将是具有挑战性的合成其他方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Diastereoselective, photocatalytic [2 + 2] dimerizations of alkenylboronic acids promoted by sugar alcohols

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Diastereoselective, photocatalytic [2 + 2] dimerizations of alkenylboronic acids promoted by sugar alcohols

In the presence of the sugar alcohol meso-erythritol, trans-2-arylvinylboronic acids undergo regio- and diastereoselective, photocatalytic [2 + 2] cycloadditions, generating all-trans-substituted cyclobutane-1,2-bis(boronic acid) derivatives. A covalent templating mechanism is proposed, involving in situ formation of a 2:1 boronic acid:tetraol adduct – likely a mixed boronic ester/hemiboronic ester. The protocol has been applied to various substituted trans-2-arylvinylboronic acid derivatives, providing access to chiral, C2-symmetric cyclobutane derivatives that would be challenging to synthesize by other means.

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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.