The substitution of hexabromomethylbenzene with 1-adamantyl carboxylate quantitatively leads to the corresponding hexacyl derivative via anchimeric assistance by the alkylcarboxy substituents.
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A Prebiotic Route to Lactate from Acetaldehyde, Cyanide and Carbon Dioxide.
Chemistry
December 2024
University of Copenhagen, Chemistry, Universitetsparken 5, Kemisk Institut, 2100, Copenhagen, DENMARK.
The atmospheric concentration of carbon dioxide (CO2) has fluctuated throughout Earth's history. However, the role of CO2 in prebiotic chemistry has predominantly been limitedly postulated as a C1 precursor, which can be reduced to carbon monoxide or methane mimicking the Wood-Ljungdahl pathway. Herein we present neglected roles of CO2 as an active promoter in accessing biologically important C3-builidng blocks such as lactate, via redox-economic reaction cycles from cyanide (C1) and acetaldehyde (C2).
View Article and Find Full Text PDFStereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.
Commun Chem
November 2024
Department of Chemistry, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
Alteration of a well-established reaction mechanism for access to different molecular structures is an inherently intriguing research subject. In that context, syn-stereospecific alkene dihalogenation draws attention as a long-standing problem in synthetic organic chemistry. The simplest approach would be the incorporation of an additional stereo-inverting step within the traditional anti-dihalogenation process.
View Article and Find Full Text PDFThe stability and hydrolytic behavior of squaramate esters in aqueous solutions have been investigated. The structure of squaramates and the nature of adjacent groups significantly influence their aqueous stability and reactivity towards nucleophiles. Squaramate esters, lacking or containing weakly basic neighboring group participation (NGP) substitutions, remain stable up to pH 9.
View Article and Find Full Text PDFSynthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.
J Org Chem
September 2024
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States.
Synthesis of an antigenic tetrasaccharide repeating unit of the -polysaccharide of lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl -1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.
View Article and Find Full Text PDFDihydrophenanthrene Open-Shell Singlet Diradicals and Their Roles in the Mallory Photocyclization Reaction.
J Am Chem Soc
January 2024
Department of Chemistry, University of Wyoming, Laramie, Wyoming 82071, United States.
A computational study (ωB97X-D/6-31G(d)) of the Mallory photocyclization reaction has revealed that the well-established dihydrophenanthrene (DHP) intermediates can adopt either closed-shell (CS) or open-shell-diradical (OS) singlet ground states. A detailed study of the properties of DHPs allowed their classifications as OS, borderline-OS, borderline-CS, or CS intermediates. The triplet electronic state and higher energy CS* isomer of all the OS singlet diradicals were computationally located, and the expected relationship between the diradical index, , and the triplet energy and the OS-CS* energy gaps was established.
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