光氧化还原催化中的对映选择性抗衡阴离子：不对称阳离子自由基狄尔斯-阿尔德反应
Enantioselective counter-anions in photoredox catalysis: the asymmetric cation radical Diels-Alder reaction.
作者信息
Morse Peter D, Nguyen Tien M, Cruz Cole L, Nicewicz David A
机构信息
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
出版信息
Tetrahedron. 2018 Jun 28;74(26):3266-3272. doi: 10.1016/j.tet.2018.03.052. Epub 2018 Mar 26.
Abstract
Control of absolute stereochemistry in radical and ion radical transformations is a major challenge in synthetic chemistry. Herein, we report the design of a photoredox catalyst system comprised of an oxidizing pyrilium salt bearing a chiral triflyl phosphoramide anion. This class of chiral organic photoredox catalysts is able to catalyze the formation of cation radical-mediated Diels-Alder transformations in up to 75:25 e.r. in both intramolecular and intermolecular examples.
摘要
在自由基和离子自由基转化中控制绝对立体化学是合成化学中的一项重大挑战。在此，我们报告了一种光氧化还原催化剂体系的设计，该体系由带有手性三氟甲磺酸磷酰胺阴离子的氧化吡喃鎓盐组成。这类手性有机光氧化还原催化剂能够在分子内和分子间的实例中催化阳离子自由基介导的狄尔斯-阿尔德转化，对映体过量比高达75:25。
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