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Stereoselective Ring-Opening Reaction of α-Fluorinated Oxetanes: A Practical and Theoretical Investigation.
J Org Chem
December 2024
Université de Caen Normandie, ENSICAEN, CNRS, LCMT, Normandie University, 6 Bd. du Maréchal Juin, Caen 14050, France.
The ring-opening reaction of fluorinated oxetanes by halides, including alkylidene oxetanes and spirocyclic oxetanes, was highly stereoselective and directed by the presence of a fluorine atom. This reaction allowed a stereoselective preparation of tetrasubstituted alkenes and substituted pyrrolidines containing all-carbon quaternary centers. Theoretical calculations were performed to shed light on experimentally observed regioselectivity in the opening of oxetane derivatives.
View Article and Find Full Text PDFDriving -butyl axial: the surprising cyclopropyl effect.
Chem Sci
October 2024
Department of Chemistry, McGill University 801 SherbrookeW. H3A 0B8 Montreal QC Canada
The presence of a small spirocyclic ring at an adjacent position alters the conformational preference for equatorial substitution in six-membered rings. DFT calculations and low-temperature H NMR experiments demonstrate that alkyl groups larger than methyl possess negative A-values when geminal to a spirocyclopropane, with larger groups such as isopropyl and -butyl being exclusively axial at -78 °C. Similar effects are found for heteroatoms, including halogens, and for a range of other electron-withdrawing substituents.
View Article and Find Full Text PDFComputational study of an oxetane 4-pyrazole as a Diels-Alder diene.
Tetrahedron Lett
October 2023
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139-4307, USA.
We combine the effects of spirocyclization and hyperconjugation to increase the Diels-Alder reactivity of the 4-pyrazole scaffold. A density functional theory (DFT) investigation predicts that 4-pyrazoles containing an oxetane functionality at the saturated center are extremely reactive despite having a relatively high-lying lowest unoccupied molecular orbital (LUMO) energy.
View Article and Find Full Text PDFPhotoinduced Temperature-Regulated Selective Carbene C-H Insertion for the Synthesis of Functionalized Spiro-β-lactones and -lactams.
Org Lett
July 2023
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
A temperature-regulated catalyst-free photoinduced selective carbene C-H insertion strategy was realized to efficiently synthesize spiro--lactones and -lactams, which hold considerable promise in drug discovery programs. The reaction shows broad applicability across a range of α-diazo esters and amides with various ring sizes and substituents and has been demonstrated to successfully achieve the late-stage spirocyclization of natural/bioactive compounds. The obtained products could be transformed into spiro-oxetanes, -azetidines, and -cyclopropanes, privileged scaffolds with broad utility in medicinal chemistry.
View Article and Find Full Text PDFGeneral Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Isosteres.
Angew Chem Int Ed Engl
September 2023
Enamine Ltd., Chervonotkatska 60, 02094, Kyiv, Ukraine.
A general approach to 3-azabicyclo[3.1.1]heptanes by reduction of spirocyclic oxetanyl nitriles was developed.
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