119330-07-3Relevant academic research and scientific papers
L-Valine derived chiral N-sulfinamides as effective organocatalysts for the asymmetric hydrosilylation of N-alkyl and N-aryl protected ketimines
Wang, Chao,Wu, Xinjun,Zhou, Li,Sun, Jian
, p. 577 - 582 (2015/02/02)
l-Valine derived N-sulfinamides have been developed as efficient enantioselective Lewis basic organocatalysts for the asymmetric reduction of N-aryl and N-alkyl ketimines with trichlorosilane. Catalyst 3c afforded up to 99% yield and 96% ee in the reduction of N-alkyl ketimines and up to 98% yield and 98% ee in the reduction of N-aryl ketimines.
Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane
Malkov, Andrei V.,Ston?ius, Sigitas,MacDougall, Kenneth N.,Mariani, Andrea,McGeoch, Grant D.,Ko?ovsky, Pavel
, p. 264 - 284 (2007/10/03)
Asymmetric reduction of N-aryl ketimines 1a-k, 43, and 45 with trichlorosilane can be catalyzed by new N-methyl l-amino acid-derived Lewis-basic organocatalysts, such as the valine-derived bisamide 3d (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure-reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i-Pr vs Me, as in 3d and 6e), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene-arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology.
CHIRAL LIGANDS CONTAINING HETEROATOMS. II. MODIFIED LITHIUM ALUMINIUM HYDRIDE REAGENTS FROM CHIRAL 1,2-DIAMINOETHANES
Falorni, Massimo,Lardicci, Luciano,Giacomelli, Giampaolo
, p. 573 - 576 (2007/10/02)
Procedures for the preparation of N-methyl-N'--1,2-diaminoethane, N-methyl-N'--1,2-diaminoethane and (S)-N-methyl-N'-phenyl-1-isopropyl-1,2-diaminoethane are reported.The stereochemistry of the products obtained by amine-m
