75472-76-3Relevant academic research and scientific papers
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
supporting information, (2020/06/17)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
P-Stereogenic and Non-P-Stereogenic Ir-MaxPHOX in the Asymmetric Hydrogenation of N -Aryl Imines. Isolation and X-ray Analysis of Imine Iridacycles
Salomó, Ernest,Rojo, Pep,Hernández-Lladó, Pol,Riera, Antoni,Verdaguer, Xavier
, p. 4618 - 4627 (2018/04/26)
A small library of Ir-MaxPHOX catalysts has been applied to the asymmetric hydrogenation of N-aryl imines. A structure-activity analysis of the three-chiral-center MaxPHOX ligand has been performed. Using complex 1b, the hydrogenation of N-aryl imines too
Solid Supported Chiral N-Picolylimidazolidinones: Recyclable Catalysts for the Enantioselective, Metal- and Hydrogen-Free Reduction of Imines in Batch and in Flow Mode
Porta, Riccardo,Benaglia, Maurizio,Annunziata, Rita,Puglisi, Alessandra,Celentano, Giuseppe
supporting information, p. 2375 - 2382 (2017/07/22)
A new class of solid supported chiral imidazolidinone organocatalysts for the catalytic reduction of imines with trichlorosilane has been developed. Polystyrene proved to be a more effective support than silica in terms of both chemical and stereochemical
Decrypting Transition States by Light: Photoisomerization as a Mechanistic Tool in Br?nsted Acid Catalysis
Renzi, Polyssena,Hioe, Johnny,Gschwind, Ruth M.
, p. 6752 - 6760 (2017/05/29)
Despite the wide applicability of enantioselective Br?nsted acid catalysis, experimental insight into transition states is very rare, and most of the mechanistic knowledge is gained by theoretical calculations. Here, we present an alternative approach (de
Chiral dienes as "ligands" for borane-catalyzed metal-free asymmetric hydrogenation of imines
Liu, Yongbing,Du, Haifeng
supporting information, p. 6810 - 6813 (2013/06/05)
This paper describes a highly enantioselective metal-free hydrogenation of imines using chiral dienes as "ligands" for the generation of catalysts with HB(C6F5)2 by hydroboration in situ to furnish a variety of chiral amin
A highly enantioselective Lewis basic organocatalyst for reduction of N-aryl imines with unprecedented substrate spectrum
Wang, Zhouyu,Ye, Xiaoxia,Wei, Siyu,Wu, Pengcheng,Zhang, Anjiang,Sun, Jian
, p. 999 - 1001 (2007/10/03)
L-Pipecolinic acid derived formamides have been developed as highly efficient and enantioselective Lewis basic organocatalysts for the reduction of N-aryl imines with trichlorosilane. Catalyst 4b afforded high isolated yields (up to 98%) and enantioselect
Supramolecular catalysis of Strecker reaction in water under neutral conditions in the presence of β-cyclodextrin
Surendra,Srilakshmi Krishnaveni,Mahesh,Rama Rao
, p. 2532 - 2534 (2007/10/03)
An environmentally benign and highly efficient procedure for the nucleophilic addition of trimethylsilyl cyanide to imines (Strecker reaction) has been developed under biomimetic conditions in water in the presence of β-cyclodextrin to afford α-aminonitriles in quantitative yields. The use of cyclodextrin precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.
L-piperazine-2-carboxylic acid derived N-formamide as a highly enantioselective Lewis basic catalyst for hydrosilylation of N-aryl imines with an unprecedented substrate profile
Wang, Zhouyu,Cheng, Mounuo,Wu, Pengcheng,Wei, Siyu,Sun, Jian
, p. 3045 - 3048 (2007/10/03)
L-Piperazine-2-carboxylic acid derived N-formamides have been developed as highly enantioselective Lewis basic catalysts for the hydrosilylation of N-aryl imines with trichlorosilane. The arene sulfonyl group on N4 was found to be critical for the high en
S-chiral sulfinamides as highly enantioselective organocatalysts
Pei, Dong,Wang, Zhouyu,Wei, Siyu,Zhang, Yu,Sun, Jian
, p. 5913 - 5915 (2007/10/03)
(Diagram presented) Easily accessible chiral sulfinamide 2 has been developed as the first highly efficient and enantioselective organocatalyst relying solely on a chiral sulfur center for stereochemical induction. In the presence of 20 mol % of 2, a broa
Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane
Malkov, Andrei V.,Mariani, Andrea,MacDougall, Kenneth N.,Kocovsky, Pavel
, p. 2253 - 2256 (2007/10/03)
Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst and the incoming imine as the main factor determining the enantiofacial selectivity.
