141565-14-2Relevant 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.
Free-radical reaction of imine derivatives in water
Miyabe, Hideto,Ueda, Masafumi,Naito, Takeaki
, p. 5043 - 5047 (2007/10/03)
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NOVEL E-Z EQUILIBRIUM OF N-ALKYL-α-ALKOXYCARBONYLNITRONE IN SOLUTION
Inouye, Yoshinobu,Hara, Junko,Kakisawa, Hiroshi
, p. 1407 - 1410 (2007/10/02)
Four N-alkyl-α-alkoxycarbonylnitrone were prepared and their NMR specra in C6D6, CDCl3, or CD3SOCD3 were measured.From the analyses of the spectra, it was found that the nitrones exhibited a facile equilibrium in all solvents used and E/Z ratio in equilibrium depended largely on the polarity of the solvent.