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An argument for abandoning the "allowed" and "forbidden" classification of electrocyclic reactions.
Chem Sci
March 2025
School of Chemistry, Cardiff University CF10 3AT UK
The division of electrocyclic reactions into "allowed" and "forbidden" classes carries the implication that reactions of the latter class are so energetically penalised that they will occur only if their "allowed" alternatives are rendered effectively impossible. The present work tests that assumption, using NEVPT2 and DFT calculations on a variety of cyclobutene ring openings and ()-1,3,5-hexatriene ring closures, and their benzannelated congeners. The results show the assumption to be incorrect.
View Article and Find Full Text PDFAllylboration of Ketones Catalyzed by BINOL Derivatives: Which Species Are Involved Depending on Substrate Reactivity?
J Org Chem
September 2024
Université de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) UMR 6226, 263 Avenue du Général Leclerc, Campus de Beaulieu, F-35000 Rennes, France.
Allylboration reactions of ketones catalyzed by BINOL derivatives can exhibit highly variable stereochemical courses depending on the nature and reactivity of the ketone substrate. In this Article, we put into perspective the relationship between the nature of the starting material and the active species involved in the asymmetric allyboration catalyzed by BINOL derivatives. This work, aimed at comparing different plausible mechanisms by density functional theory (DFT) at the M06-2X/6-311+G(d,p) level involving different types of allylboronates in the presence of the organocatalyst, leads to the confirmation of the hitherto accepted hypothesis of a reaction promoted by the transient cyclic allyl-1,3,2-dioxaborolane derived from BINOLs in the case of unactivated or weakly activated ketones such as indanone.
View Article and Find Full Text PDFInvestigating the Origin of Epimerization Attenuation during Pd-Catalyzed Cross-Coupling Reactions.
ACS Catal
August 2024
Department of Chemistry, The University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada.
Palladium-catalyzed cross-couplings remain among the most robust methodologies to form carbon-carbon and carbon-heteroatom bonds. In particular, carbon-nitrogen (C-N) couplings (Buchwald-Hartwig aminations) find widespread use in fine chemicals industries. The use of base in these reactions is critical for catalyst activation and proton sequestration.
View Article and Find Full Text PDFStructural Chemistry of C-N Axially Chiral Compounds.
J Org Chem
August 2024
Chemistry and Materials Program, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo, 135-8548, Japan.
In the last several years, atropisomers owing to the rotational restriction around a C-N single bond (C-N axially chiral compounds) have attracted significant attention in the field of synthetic organic chemistry. In particular, the highly enantioselective synthesis of various C-N axially chiral compounds and their application to asymmetric reactions have been reported by many groups. On the other hand, studies on the structural chemistry of C-N axially chiral compounds have attracted scant attention in comparison with synthetic studies.
View Article and Find Full Text PDFNon-enantioselective, enantioselective, and two-dimensional liquid chromatography coupled with tandem mass spectrometry for the study of stereochemical disposition of oxylipins in cGMP-regulated hemin-treated platelets.
J Pharm Biomed Anal
September 2024
University of Tübingen, Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, Auf der Morgenstelle 8, Tübingen 72076, Germany. Electronic address:
Oxylipins are important low abundant signaling molecules in living organisms. In platelets they play a primary role in platelet activation and aggregation in the course of thrombotic events. In vivo, they are enzymatically synthesized by cyclooxygenases, lipoxygenases, or cytochrome P450 isoenzmes, resulting in diverse polyunsaturated fatty acid (FA) metabolites including hydroxy-, epoxy-, oxo-FAs, and endoperoxides with pro-thrombotic or anti-thrombotic effects.
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