We introduce a new strategy for synthesis of chiral amines: couplings of α-aminoalkyl nucleophiles generated by enantioselective migratory insertion of 2-azadienes to a Cu-H. In this report, we demonstrate its application in catalytic reductive coupling of 2-azadienes and ketones to furnish 1,2-amino tertiary alcohols with vicinal stereogenic centers.
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http://dx.doi.org/10.1021/jacs.7b12213 | DOI Listing |
J Am Chem Soc
January 2025
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.
Carboranyl amines are distinct from typical organic amines. Due to the electronic influence of the carborane cage, they have low nucleophilicity and are reluctant to alkylate. Moreover, asymmetric synthesis of chiral carboranes is still in its infancy.
View Article and Find Full Text PDFChirality
January 2025
State Key Laboratory of Food Science and Resources, Jiangnan University, Wuxi, Jiangsu, China.
Efficient enantioselective separation is a critical process in pharmaceutical and chemical industries for the production of chiral compounds. Herein, we developed a novel approach for the efficient enantioselective separation of primary amines using supercritical fluid chromatography (SFC) with a commercially available SFC column, Cel1. The key factors of separation, including cosolvent ratios, total cosolvent percentages, and temperature, were systematically assessed in this study.
View Article and Find Full Text PDFAnal Chim Acta
February 2025
Institute of Physical and Analytical Chemistry, School of Exact and Natural Sciences, Tbilisi State University, 0179, Tbilisi, Georgia. Electronic address:
Background: Isotopologues resulting from the labelling of molecules with deuterium have attracted interest due to the isotope effect observed in chemistry and biosciences. Isotope effect may also play out in noncovalent interactions and mechanisms leading to intermolecular recognition. In chromatography, differences in retention time between isotopologues, as well as between isotopomers have been observed resulting in two different elution sequences (isotope effects): the normal isotope effect when heavier isotopologues retain longer than lighter analogues, and the inverse isotope effect featuring the opposite elution order.
View Article and Find Full Text PDFAnal Chim Acta
February 2025
Key Laboratory of Molecular Medicine and Biotherapy, School of Life Science, Beijing Institute of Technology, No. 5 Zhongguancun South Street, Beijing, 100081, China. Electronic address:
Background: The metal organic cages (MOCs) are an emerging type of porous material that has attracted considerable research interest due to their unique properties, including good stability and well-defined intrinsic cavities. The chiral MOCs with porous structures have broad application prospects in enantiomeric recognition and separation. However, there are almost no relevant reports on chiral MOCs as chiral stationary phases (CSPs) for enantioseparation by high-performance liquid chromatography (HPLC).
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
School of Life Sciences and Biopharmaceutical Sciences, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe, Shenyang 110016, People's Republic of China. Electronic address:
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