141410-06-2Relevant articles and documents
A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
Pollastrini, Matteo,Lipparini, Filippo,Pasquinelli, Luca,Balzano, Federica,Barretta, Gloria Uccello,Pescitelli, Gennaro,Angelici, Gaetano
, p. 7946 - 7954 (2021/06/28)
A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.
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.
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
