146495-24-1Relevant articles and documents
Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates
Ezawa, Tetsuya,Sohtome, Yoshihiro,Hashizume, Daisuke,Adachi, Masaya,Akakabe, Mai,Koshino, Hiroyuki,Sodeoka, Mikiko
supporting information, p. 9094 - 9104 (2021/07/01)
Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.
Organocatalytic enantio- and diastereoselective 1,3-dipolar cycloaddition between alanine-derived ketonitrones and E-crotonaldehyde: Efficiency and full stereochemical studies
Selim, Khalid B.,Beauchard, Anne,Lhoste, Jér?me,Martel, Arnaud,Laurent, Mathieu Y.,Dujardin, Gilles
, p. 1670 - 1677 (2013/02/23)
Highly enantio- and exo-selective 1,3-dipolar cycloadditions of alanine-derived ketonitrones to E-crotonaldehyde could be realized in a good yield by the use of a chiral imidazolidinone salt without the addition of water. The origin of the stereoselectivi
Photoreduction of imines. An environmentally friendly approach to obtain amines
Ortega, María,Rodríguez, Miguel A.,Campos, Pedro J.
, p. 11686 - 11691 (2007/10/03)
The photoreduction of different imines to amines in alcoholic solvents is reported. The reduction involves a versatile and chemoselective methodology that is environmentally friendly in that it avoids the use of metal hydrides and other dangerous reducing agents.