Steric and electronic tuning of atropisomeric amino alcohol type ligands with a 1-arylpyrrole backbone
Szilvia Deák,Béla Mátravölgyi,Gyula Feczku,Zsuzsa Erdélyi,Miklos Nyerges,Ferenc Faigl,Ferenc Faigl +6 more
Reads0
Chats0
TLDR
In this paper, the synthesis of trifluoromethyl group containing atropisomeric amino alcohols and their application in enantioselective diethylzinc additions to aldehydes is described.Abstract:
The synthesis of new, trifluoromethyl group containing atropisomeric amino alcohols and their application in enantioselective diethylzinc additions to aldehydes is described. A significant improvement of the enantioinductive effects of the new ligands by increasing the Bronsted acidity and bulkiness of the triarylcarbinol moiety is also reported. Tuning was achieved by the introduction of phenyl substituents containing two trifluoromethyl groups onto the α-carbon of the tertiary alcohol part of the ligand. The application of the new catalysts provided 1-(substituted phenyl)propanols with excellent enantiomeric purities.read more
Citations
More filters
Journal ArticleDOI
Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles
TL;DR: The atroposelective synthesis of axially chiral arylpyrrole derivatives proved to be efficient chiral ligands for asymmetric catalysis, through desymmetrization and kinetic resolution.
Journal ArticleDOI
Asymmetric Construction of Axially Chiral 2-Arylpyrroles by Chirality Transfer of Atropisomeric Alkenes
TL;DR: A novel heterocyclic 2-arylazepine atropisomer was realized through a rationally designed ene reaction, affording novel atrop isomers with fully substituted pyrrole moiety in high enantiopurities.
Journal ArticleDOI
Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis.
TL;DR: DFT calculations elucidate the origins of the observed excellent atroposelectivity in N‐arylpyrroles and reveal the synthetic utility of this new method.
Journal ArticleDOI
Organocatalytic Cascade β-Functionalization/Aromatization of Pyrrolidines via Double Hydride Transfer.
TL;DR: The deuterium-labeling experiments indicate that sequential double hydride transfer processes serve as the key steps in this transformation of N-arylpyrrolidines into β-substituted arylpyrroles.
Journal ArticleDOI
Access to Fluorazones by Intramolecular Dehydrative Cyclization of Aromatic Tertiary Amides: A Synthetic and Mechanistic Study.
TL;DR: The findings that Tf2O-mediated amide activation is obstructed by the easy protonation of amides by the formed triflic acid during the activation step are reported.
References
More filters
Journal ArticleDOI
Enantioselective addition of organozinc reagents to aldehydes
Kenso Soai,Seiji Niwa +1 more
Journal ArticleDOI
Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification†
Ryoji Noyori,Masato Kitamura +1 more
TL;DR: In this paper, an enantioselective alkylation of aldehydes using diastereomeric (homochiral and heterochiral) dinuclear complexes formed from the dialkylzinc and the DAIB auxiliary is described.
Journal ArticleDOI
Catalytic Asymmetric Organozinc Additions to Carbonyl Compounds
Lin Pu,Hong-Bin Yu +1 more
TL;DR: These studies on macromolecular chiral catalysts demonstrate that these materials are potentially very useful for practical applications and can also be preserved in the rigid and sterically regular polymer provided the catalytically active species of the monomer catalyst is not its aggregate.
Journal ArticleDOI
Enantioselective addition of diethylzinc to benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols
Nobuki Oguni,Takao Omi +1 more
TL;DR: The reaction of diethylzinc with benzaldehyde catalyzed by a small amount of chiral 2-amino-1-alcohols in toluene at room temperature gave optically active 1-phenylpropan-1ol almost quantitatively in ∼, 50% ee as discussed by the authors.