硼酸酯促进的临时配位[2+2]环加成反应：阿托查敏 J 和胡椒基硼烷 B 的合成。
Boronic Ester Enabled [2 + 2]-Cycloadditions by Temporary Coordination: Synthesis of Artochamin J and Piperarborenine B.
机构信息
Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States.
出版信息
J Am Chem Soc. 2022 Oct 19;144(41):18790-18796. doi: 10.1021/jacs.2c08777. Epub 2022 Oct 6.
Abstract
A strategy for the photosensitized cycloaddition of alkenylboronates and allylic alcohols by a temporary coordination is presented. The process allows for the synthesis of a diverse range of cyclobutylboronates. Key to development of these reactions is the temporary coordination of the allylic alcohol to the Bpin unit. This not only allows for the reaction to proceed in an intramolecular manner but also allows for high levels of stereo and regiocontrol. A key aspect of these studies is the utility of the cycloadducts in the synthesis of complex natural products artochamin J and piperarborenine B.
摘要
提出了一种通过暂时配位实现烯基硼酸酯和烯丙醇的光致敏环加成的策略。该过程允许合成各种环丁基硼酸酯。这些反应的关键是烯丙醇与 Bpin 单元的暂时配位。这不仅允许反应以分子内方式进行，还允许高水平的立体和区域控制。这些研究的一个关键方面是环加成物在复杂天然产物 artochamin J 和 piperarborenine B 合成中的应用。
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