钯催化烯醇盐的烯烃双官能团化反应用于合成取代双环环戊烷。
Pd-Catalyzed Alkene Difunctionalization Reactions of Enolates for the Synthesis of Substituted Bicyclic Cyclopentanes.
作者信息
Bornowski Evan C, Hinds Elsa M, White Derick R, Nakamura Yusuke, Wolfe John P
机构信息
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan, 48109-1055, United States.
出版信息
Org Process Res Dev. 2019 Aug 16;23(8):1610-1630. doi: 10.1021/acs.oprd.9b00248. Epub 2019 Jul 30.
Abstract
Palladium-catalyzed alkene difunctionalization reactions between alkenes bearing tethered aryl or alkenyl triflates and enolate nucleophiles are described. The transformations form two C-C bonds, a ring, and up to two stereocenters, while producing substituted cyclopentane derivatives that contain appended carbonyl functionality. Products are formed with up to >20:1 diastereoselectivity, and formation of sterically congested bonds between quaternary carbon atoms is feasible.
摘要
描述了钯催化的带有连接芳基或烯基三氟甲磺酸酯的烯烃与烯醇盐亲核试剂之间的烯烃双官能化反应。这些转化形成了两个C-C键、一个环和多达两个立体中心，同时生成含有附加羰基官能团的取代环戊烷衍生物。产物以高达>20:1的非对映选择性形成，并且在季碳原子之间形成空间拥挤的键是可行的。
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2
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J Org Chem. 2018 Nov 2;83(21):13568-13573. doi: 10.1021/acs.joc.8b02165. Epub 2018 Oct 10.
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J Am Chem Soc. 2018 Oct 3;140(39):12364-12368. doi: 10.1021/jacs.8b08190. Epub 2018 Sep 24.
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