35341-74-3Relevant academic research and scientific papers
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.
Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations
Capraro, Maria Grazia,Franchi, Paola,Lanzalunga, Osvaldo,Lapi, Andrea,Lucarini, Marco
, p. 6435 - 6443 (2014/08/05)
Chiral N-hydroxybenzamides (1H-3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1?-3?. The latter species have been generated by oxidation of 1H-3H with Pb(OAc)4 or hydrogen abstraction from 1H-3H by the tert-butoxyl radical and characterized by UV-vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1?-3? from three chiral benzylic substrates (1-phenylethylamine, 1-phenylethanol, and α-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 ≥ kH(S)/kH(R) ≥ 2.
BIS-PYRIDYLPYRIDONES AS MELANIN-CONCENTRATING HORMONE RECEPTOR 1 ANTAGONISTS
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Page/Page column 21-22, (2010/12/29)
The invention provides novel bis-pyridylpyridones which are antagonists at the melanin-concentrating hormone receptor 1 (MCHR1 ), pharmaceutical compositions containing them, processes for their preparation, and their use in therapy and for the treatment
Diastereoselective Diels-Alder additions of ethene to substituted homochiral 2(1H)-pyrazinones
Alen, Jo,Smets, Wim J.,Dobrzanska, Liliana,De Borggraeve, Wim M.,Compernolle, Frans,Hoornaert, Georges J.
, p. 965 - 971 (2008/02/13)
Diels-Alder reactions of ethene with 2(1H)-pyrazinones bearing a homochiral auxiliary group are presented. The cycloaddition products form with diasteromeric excesses of up to 50%. To the best of our knowledge, these are the first Diels-Alder reactions wi
