58751-83-0Relevant articles and documents
Decoding stereocontrol during the photooxygenation of oxazolidinone- functionalized enecarbamates
Solomon, Marissa R.,Sivaguru,Jockusch, Steffen,Adam, Waldemar,Turro, Nicholas J.
, p. 2142 - 2145 (2010)
Figure presented Systematically designed oxazolidinone-derived enecarbamates reveal that solvent and temperature effects on the stereoselectivity during photooxygenation are likely due to the conformational flexibility of the chiral phenethyl side chain (entropy factors); the extent of enantiomeric excess in the photoproduct is dictated by the alkene geometry.
Catalytic Reductive Cross Coupling and Enantioselective Protonation of Olefins to Construct Remote Stereocenters for Azaarenes
Kong, Manman,Tan, Yaqi,Zhao, Xiaowei,Qiao, Baokun,Tan, Choon-Hong,Cao, Shanshan,Jiang, Zhiyong
supporting information, p. 4024 - 4031 (2021/04/07)
A novel enantioselective protonation protocol that is triggered by reductive cross coupling of olefins is reported. When under cooperative photoredox and chiral hydrogen-bonding catalytic conditions and using a terminal reductant, various α-branched vinyl
Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids
Betori, Rick C.,Davies, Anna V.,Fitzpatrick, Keegan P.,Scheidt, Karl A.
supporting information, p. 9143 - 9148 (2020/03/30)
As a key element in the construction of complex organic scaffolds, the formation of C?C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C?C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.