83196-02-5Relevant academic research and scientific papers
Direct C(sp3)-N Radical Coupling: Photocatalytic C-H Functionalization by Unconventional Intermolecular Hydrogen Atom Transfer to Aryl Radical
Cho, Eun Jin,Hwang, Ho Seong,Kang, Jihee,Soni, Vineet Kumar
, (2020/08/12)
An unconventional approach for intermolecular direct C(sp3)-N radical coupling has been developed by photocatalytic C(sp3)-H activation of simple alkyl substrates using O-benzoyl oximes. The selective photocatalytic energy-transfer-driven homolysis followed by decarboxylation generates the persistent iminyl radical and aryl radical, which would undergo an unprecedented intermolecular hydrogen atom abstraction from the alkyl substrate to provide the key C(sp3) radical. Selective radical-radical C-N cross-coupling furnishes imines which are valuable amine building blocks.
Synthesis Applications of Cationic Aza-Cope Rearrangements. Stereoselective synthesis of cis- and trans-3a-Aryl-4-oxodecahydrocycloheptapyrroles
Overman, Larry E.,Jacobsen E. Jon,Doedens, Robert J.
, p. 3393 - 3400 (2007/10/02)
A general synthesis of 3a-aryl-4-oxodecahydrocycloheptapyrroles is detailed (eq 1, n=2).The key step is a "ring-enlarging pyrrolidine annulation" reaction which occurs when 2-amino-1-(1-arylvinyl)cyclohexanols are treated at 25-80 deg C with an aldehyde and acid.Three different methods (Schemes I and II) for assembling the 2-amino-1-(1-arylvinyl)cyclohexanol intermediates are reported. cis-3a-Aryl-4-oxodecahydrocycloheptapyrroles can be formed with complete stereocontrol from either cis- or trans-2-amino-1-(1-arylvinyl)cyclohexanols.The corresponding trans bicyclics can be prepared with modest (ca. 3:1) selectivity from cis-2--1-(1-arylvinyl)cyclohexanols.The stereochemical outcome of these tandem cationic aza-Cope-Mannich cyclization reactions is consistent with chair topographies for the rearrangment steps (Scheme III).
SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS. STEREOCONTROLLED SYNTHESIS OF CYCLOHEPTAPYRROLIDINES
Overman, Larry E.,Jacobsen, E. Jon
, p. 2737 - 2740 (2007/10/02)
Both cis- and trans-3a-aryl-4-oxo-decahydrocycloheptapyrroles can be prepared in stereocontrolled fashions by the reaction of 2-amino-1-(1-phenylvinyl)cyclohexanols with formaldehyde and acid.
