141410-06-2Relevant articles and documents
Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
Song, Geyang,Yang, Liu,Li, Jing-Sheng,Tang, Wei-Jun,Zhang, Wei,Cao, Rui,Wang, Chao,Xiao, Jianliang,Xue, Dong
supporting information, p. 21536 - 21542 (2021/08/23)
The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.
Promoting the Furan Ring-Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol
Clerc, Michèle,Stricker, Friedrich,Ulrich, Sebastian,Sroda, Miranda,Bruns, Nico,Boesel, Luciano F.,Read de Alaniz, Javier
supporting information, p. 10219 - 10227 (2021/03/22)
Donor–acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, ma
Enantioselective Reformatsky Reaction of Ketones Catalyzed by Chiral Indolinylmethanol
Luo, Renshi,Chen, Miao-Miao,Ouyang, Lu,Chan, Albert S. C.,Lu, Gui
supporting information, p. 4805 - 4811 (2020/07/14)
A reliable and practical Reformatsky reaction of ethyl iodide acetate with ketones for the synthesis of chiral β-hydroxyl carbonyl compounds in good yields and excellent enantioselectivities is presented. A readily available dihydroindole derivative was u