61451-86-3

Upstream product

• 3433-56-5 1-(1-phenylvinyl)pyrrolidine 
• 694-53-1 phenylsilane 
• 123-75-1 pyrrolidine 
• 98-86-2 acetophenone 
• 110-63-4 Butane-1,4-diol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 110-52-1 1,4-dibromo-butane 

Downstream Products

• 172842-11-4 (R,R)-bis<2-<1-(pyrrolidin-1-yl)ethyl>phenyl> diselenide 

Relevant academic research and scientific papers

Rhodium catalysts derived from a fluorinated phanephos ligand are highly active catalysts for direct asymmetric reductive amination of secondary amines

An asymmetric hydrogenation of enamines is efficiently catalysed by rhodium complexed with a fluorinated version of the planar chiral paracyclophane-diphosphine ligand, Phanephos. This catalyst was shown to be very active, with examples operating at just

Secondary amines as coupling partners in direct catalytic asymmetric reductive amination

The secondary amine participating asymmetric reductive amination remains an unsolved problem in organic synthesis. Here we show for the first time that secondary amines are capable of effectively serving as N-sources in direct asymmetric reductive amination to afford corresponding tertiary chiral amines with the help of a selected additive set under mild conditions (0-25 °C). The applied chiral phosphoramidite ligands are readily prepared from BINOL and easily modified. Compared with common tertiary chiral amine synthetic methods, this procedure is much more concise and scalable, as exemplified by the facile synthesis of rivastigmine and N-methyl-1-phenylethanamine.

Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols

A series of o-xylylene-type 1,4-amino alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since the stereochemical outcome of the reaction was controlled by the chiral benzylic carbon bearing amino group. Highest catalytic activity was obtained by using (R)-1-{2-[1-(pyrrolidin-1-yl)ethyl]phenyl}cyclohexan-1-ol (1n) derived from (R)-1-(1-phenylethyl)pyrrolidine and cyclohexanone. Various chiral secondary alcohols were obtained by the reaction of diethylzinc and aldehydes in the presence of 1n within 2 h with good to high enantioselectivities.

Chiral molecular tweezers: Synthesis and reactivity in asymmetric hydrogenation

We report the synthesis and reactivity of a chiral aminoborane displaying both rapid and reversible H2 activation. The catalyst shows exceptional reactivity in asymmetric hydrogenation of enamines and unhindered imines with stereoselectivities of up to 99% ee. DFT analysis of the reaction mechanism pointed to the importance of both repulsive steric and stabilizing intermolecular non-covalent forces in the stereodetermining hydride transfer step of the catalytic cycle.

Borrowing hydrogen methodology for amine synthesis under solvent-free microwave conditions

Application of microwave heating to the Borrowing Hydrogen strategy to form C-N bonds from alcohols and amines is presented, removing the need for solvent and reducing the reaction times while still yielding results comparable with those using thermal heating.

Asymmetric hydrogenation of unfunctionalized enamines catalyzed by iridium complexes of chiral spiro N,N-diarylphosphoramidites

Chiral spiro N,N-diarylphosphoramidites were synthesized. These new chiral spiro monophosphoramidites were efficient ligands for iridium-catalyzed asymmetric hydrogenation of unfunctionalized enamines derived from simple alkyl aryl ketones, providing chiral tertiary amines in good enantioselectivities (up to 90% ee).

Iridium-catalyzed asymmetric hydrogenation of unfunctionalized enamines

The application of cationic iridium catalysts with chiral oxazoline- or pyridine-based N,P ligands for the asymmetric hydrogenation of different unfunctionalized enamines was reported. N-methyl-N-phenyl- and N-methyl-N-benzly-(1-phynylvinly1)amine were hy

Access to chiral tertiary amines via the iridium-catalyzed asymmetric hydrogenation of enamines

The asymmetric hydrogenation of N,N-dialkyl and N-alkyl-N-aryl enamines to chiral tertiary amines was studied. All the N,P-ligated iridium complexes investigated were active catalysts for the reaction, but only those with bicycle-supported oxazoline-phosp

First detection of a selenenyl fluoride ArSe-F by NMR spectroscopy: The nature of Ar2Se2/XeF2 and ArSe-SiMe 3/XeF2 reagents

Arylselenenyl fluorides ArSeF are obtained from diselenides Ar 2Se2 or arylselenotrimethylsilanes ArSe-SiMe3, and XeF2. They are detected by low-temperature 19F and 77Se NMR spectroscopy. Substitution in the ortho position of the aromatic ring to provide electronic or steric protection is a requirement for their formation. ArSe-F compounds decompose according to 3 ArSe-F → [ArSe-SeF2Ar] + ArSe-F- → ArSeF3 + Ar 2Se2. Reaction energies for this disproportionation as well as that of the sulfur and tellurium homologues have been calculated with MP2, CCSD(T,) and B3 LYP methods. They were found to be increasingly exothermic in the sequence S 77Se and 19F chemical shifts have been calculated by GIAO-MP2 and GIAO-B3LYP methods and are in good agreement with experimental values.

Catalytic asymmetric reduction of enamines

A catalytic asymmetric reduction process, which, by hydrogenating enamines, yields a corresponding amine having a high level of enantiomeric purity is disclosed. The reduction process utilizes a chiral metal catalyst that includes a metal or metal complex