Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.
Laboratoire Chimie Thérapeutique, Faculté de Pharmacie-Biocis 8076, LabEx LERMIT, 5, rue J.B Clément, 92296, Châtenay Malabry, France.
Angew Chem Int Ed Engl. 2020 May 25;59(22):8491-8496. doi: 10.1002/anie.202000838. Epub 2020 Mar 18.
An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent "redox" selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.
一种高效的对映选择性构建四氢萘-1,4-二酮和二氢萘-1,4-二醇的方法，通过手性磷酸催化的醌 Diels-Alder 反应与烯碳酰胺反应。二烯上保护基的性质是实现高对映选择性的关键。使用适量的醌可以控制不同的“氧化还原”选择性。通过单个氧化还原异构体，可以实现可逆的氧化还原切换而不损失对映选择性。
