500730-73-4Relevant academic research and scientific papers
Intermolecular Crossed [2 + 2] Cycloaddition Promoted by Visible-Light Triplet Photosensitization: Expedient Access to Polysubstituted 2-Oxaspiro[3.3]heptanes
Murray, Philip R. D.,Bussink, Willem M. M.,Davies, Geraint H. M.,Van Der Mei, Farid W.,Antropow, Alyssa H.,Edwards, Jacob T.,D'Agostino, Laura Akullian,Ellis, J. Michael,Hamann, Lawrence G.,Romanov-Michailidis, Fedor,Knowles, Robert R.
, p. 4055 - 4063 (2021)
This paper describes an intermolecular cross-selective [2 + 2] photocycloaddition reaction of exocyclic arylidene oxetanes, azetidines, and cyclobutanes with simple electron-deficient alkenes. The reaction takes place under mild conditions using a commercially available Ir(III) photosensitizer upon blue light irradiation. This transformation provides access to a range of polysubstituted 2-oxaspiro[3.3]heptane, 2-azaspiro[3.3]heptane, and spiro[3.3]heptane motifs, which are of prime interest in medicinal chemistry as gem-dimethyl and carbonyl bioisosteres. A variety of further transformations of the initial cycloadducts are demonstrated to highlight the versatility of the products and enable selective access to either of a syn- or an anti-diastereoisomer through kinetic or thermodynamic epimerization, respectively. Mechanistic experiments and DFT calculations suggest that this reaction proceeds through a sensitized energy transfer pathway.
Enantioselective synthesis of 2-aryl cyclopentanones by asymmetric epoxidation and epoxide rearrangement
Shen, Yu-Mei,Wang, Bin,Shi, Yian
, p. 1429 - 1432 (2007/10/03)
(Chemical Equation Presented) Optically active epoxides are prepared by the highly enantioselective epoxidation of benzylidenecyclobutanes using a glucose-derived ketone as the catalyst and oxone as the oxidant. A subsequent Lewis acid catalyzed rearrange
