Enantioselective counter-anions in photoredox catalysis: The asymmetric cation radical Diels-Alder reaction

TETRAHEDRON

卷:74

Article; Proceedings Paper

Morse, Peter D.¹  Nguyen, Tien M.¹  Cruz, Cole L.¹  Nicewicz, David A.¹ 

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

关键词: Photoredox;    Ctalysis;    Enantioselective;    Cycloaddition;    Chiral anion;   

DOI  :  10.1016/j.tet.2018.03.052

来源: Elsevier

【 摘 要 】

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 N-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. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

Free