80917-38-0Relevant academic research and scientific papers
Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides
Miyaji, Ryota,Wada, Yuuki,Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro
, p. 1518 - 1523 (2017/08/14)
Bifunctional organocatalysts bearing amino and urea functional groups in a chiral molecular skeleton were applied to the enantioselective synthesis of axially chiral benzamides via aromatic electrophilic bromination. The results demonstrate the versatilit
Bifunctional organocatalysts for the enantioselective synthesis of axially chiral isoquinoline n -oxides
Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
, p. 6766 - 6769 (2015/06/16)
Bifunctional catalysts bearing amino and urea functional groups have been applied for a novel, highly enantioselective synthesis of axially chiral isoquinoline N-oxides, which are promising chiral ligands or organocatalysts in organic synthesis. This is t
Enantioselective synthesis of atropisomeric benzamides through peptide-catalyzed bromination
Barrett, Kimberly T.,Miller, Scott J.
supporting information, p. 2963 - 2966 (2013/04/10)
We report the enantioselective synthesis of atropisomeric benzamides employing catalytic electrophilic aromatic substitution reactions involving bromination. The catalyst is a simple tetrapeptide bearing a tertiary amine that may function as a Br?nsted base. A series of tri- and dibrominations were accomplished for a range of compounds bearing differential substitution patterns. Tertiary benzamides represent appropriate substrates for the reaction since they exhibit sufficiently high barriers to racemization after ortho functionalization. Mechanism-driven experiments provided some insight into the basis for selectivity. Examination of the observed products at low conversion suggested that the initial catalytic bromination may be regioselective and stereochemistry-determining. A complex between the catalyst and substrate was observed by NMR spectroscopy, revealing a specific association. Finally, the products of these reactions may be subjected to regioselective metal-halogen exchange and trapping with I2, setting the stage for utility.
