Palladium-catalyzed dehydrosulfurative Liebeskind-Srogl coupling of terminal alkynes with 2-mercapto-1,3-pyrimidine-5-carbaldehyde under base-free conditions provides 2-(alkynyl)-1,3-pyrimidine-5-carbaldehydes, which are substrates for autocatalytic amplification of chirality according to Soai et al. The mercapto aldehyde acceptor is obtained by condensation of Arnold's vinamidinium salt with thiourea.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/ol500189s | DOI Listing |
Sci Total Environ
January 2024
Department of Pharmacy, Osaka Medical and Pharmaceutical University, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan; Faculty of Human Development, Department of Food and Nutrition Management Studies, Soai University, 4-4-1 Nankonaka, Osaka Suminoeku, Osaka 559-0033, Japan.
The emergence and spread of antimicrobial resistance (AMR) continue on a global scale. The impacts of wastewater on the environment and human health have been identified, and understanding the environmental impacts of hospital wastewater and exploring appropriate forms of treatment are major societal challenges. In the present research, we evaluated the efficacy of ozone (O)-based advanced wastewater treatment systems (O, O/HO, O/UV, and O/UV/HO) for the treatment of antimicrobials, antimicrobial-resistant bacteria (AMRB), and antimicrobial resistance genes (AMRGs) in wastewater from medical facilities.
View Article and Find Full Text PDFChirality
September 2023
Department of Chemistry, Ludwig-Maximilians-University Munich, Munich, Germany.
Soai's asymmetric autocatalysis represents a highly remarkable example for spontaneous symmetry breaking and enantioselective amplification in the enantioselective alkylation of pyrimidine-5-carbaldehydes to the corresponding chiral pyrimidine alcohols. Recently, zinc hemiacetalate complexes, formed from pyrimidine-5-carbaldehydes and the chiral product alcohol, were identified by in situ high-resolution mass spectrometric measurements as highly active transient asymmetric catalysts in this autocatalytic transformation. To study the formation of such hemiacetals and their stereodynamic properties, we focused on the synthesis of coumarin homolog biaryl systems with carbaldehyde and alcohol substituents.
View Article and Find Full Text PDFOrig Life Evol Biosph
September 2022
Department of Chemistry, Nara Women's University, Kita-Uoya Nishi-machi, Nara, 630-8506, Japan.
Biological homochirality of essential components such as L-amino acids and D-sugars is prerequisite for the emergence, evolution and the maintenance of life. Implication of biological homochirality is described. Considerable interest has been focused on the origin and the process leading to the homochirality.
View Article and Find Full Text PDFChem Asian J
August 2021
Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, 0315, Oslo, Norway.
Symmetry breaking is observed in the Soai reaction in a confinement environment provided by zirconium-based UiO-MOFs used as crystalline sponges. Subsequent reaction of encapsulated Soai aldehyde with Zn(i-Pr) vapour promoted absolute asymmetric synthesis of the corresponding alkanol. ATR-IR and NMR confirm integration of aldehyde into the porous material, and a similar localization of newly formed chiral alkanol after reaction.
View Article and Find Full Text PDFJ Am Chem Soc
October 2020
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, United States.
Diisopropylzinc alkylation of pyrimidine aldehydes-the Soai reaction, with its astonishing attribute of amplifying asymmetric autocatalysis-occupies a unique position in organic chemistry and stands as an eminent challenge for mechanistic elucidation. A new paradigm of "mixed catalyst-substrate" experiments with pyrimidine and pyridine systems allows a disconnection of catalysis from autocatalysis, providing insights into the role played by reactant and alkoxide structure. The alkynyl substituent favorably tunes catalyst solubility, aggregation, and conformation while modulating substrate reactivity and selectivity.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!