146495-24-1Relevant 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.
Divergent synthesis of α-functionalized amides through selective N-O/C-C or N-O/C-C/C-N cleavage of aza-cyclobutanone oxime esters
Liu, Hua-Wei,Wang, Dian-Liang,Jiang, Nan-Quan,Li, Hai-Yan,Cai, Zhong-Jian,Ji, Shun-Jun
, p. 9618 - 9621 (2021/09/28)
Herein, a novel sequential ring opening reaction of aza-cyclobutanone oxime esters with isocyanides is described. The reaction proceeded smoothly under redox-neutral and mild conditions, leading to a divergent synthesis of α-cyanomethylaminoamides, α-acyloxyamides and α-acylaminoamides. In these transformations, a selective N-O/C-C or N-O/C-C/C-N cleavage was achieved only by changing the iron-catalyst system. Among them, a rare sequential N-O/C-C/C-N cleavage process with a classical Passerini or Ugi multicomponent reaction can be executed in a single step. To the best of our knowledge, this work creates a novel reaction mode of cycloketone oximes and provides new opportunities for reaction design.
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.
Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation
Malkov, Andrei V.,Bourhani, Zainaba,Kocovsky, Pavel
, p. 3194 - 3200 (2007/10/03)
New sulfonamide-derived hydroxamic acids 7-11 have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to 74% ee. The Royal Society of Chemistry 2005.
A new method of N-benzhydryl deprotection in 2-azetidinone series
Laurent, Mathieu,Belmans, Marc,Kemps, Luc,Ce?re?siat, Marcel,Marchand-Brynaert, Jacqueline
, p. 570 - 576 (2007/10/03)
A mild and efficient procedure for the selective cleavage of N-benzhydryl protecting group of β-lactams is described. The protected 2-azetidinones 4, precursors of carbapenems, were treated with a stoichiometric amount of N-bromosuccinimide and a catalyti
A novel transformation of primary amines to N-monoalkylhydroxylamines
Tokuyama,Kuboyama,Amano,Yamashita,Fukuyama
, p. 1299 - 1304 (2007/10/03)
A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.
