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Relevant academic research and scientific papers

An efficient proline-based homogeneous organocatalyst with recyclability

In this work, a homogeneous organocatalyst was developed for the asymmetric reduction of imines. This catalyst could be separated by cyclodextrin-modified Fe3O4@SiO2 magnetic nanoparticles and then released back into a fre

Asymmetric hydrogenation of imines with chiral alkene-derived boron Lewis acids

With the aim of developing easily accessible chiral Lewis acids for asymmetric hydrogenation, a variety of binaphthyl-based chiral alkenes were prepared in one step from the corresponding diols. Using the in situ generated chiral boron Lewis acids through

L-Pipecolinic acid derived Lewis base organocatalyst for asymmetric reduction of N-aryl imines by trichlorosilane: Effects of the side amide group on catalytic performances

A series of N-formamides derived from pipecolinic acid have been synthesized and tested as Lewis base catalysts for the enantioselective reduction of N-aryl imines by trichlorosilane. Through the investigation of the structure-efficacy relationship between the side amide group and catalytic performance, several highly effective catalysts were discovered. In particular, arylamido-type catalyst 5i and non-arylamido-type catalyst 6c exhibited high reactivity and enantioselectivity, furnishing the reduction of a wide variety of N-aryl imines with high isolated yields (up to 98%) and ee values (up to 96%) under mild conditions. Moreover, these two catalysts complement each other in terms of their tolerances to nonaromatic ketimines and non-methyl ketimines. The Royal Society of Chemistry 2013.

Rationally-designed S-chiral bissulfinamides as highly enantioselective organocatalysts for reduction of ketimines

We recently reported the first example of S-chiral organocatalysts, that are highly efficient and enantioselective in substoichometric amounts, and which use a chiral monosulfinamide group as Lewis base to activate trichlorosilane (HSiCl3) to reduce N-arylketimines. Aplausible mechanism involving two molecules of the monosulfinamde catalyst for the activation of HSiCl 3 prompted us to design S-chiral bissulfinamides as new catalysts. We herein describe our findings that an easily prepared S-chiral bissulfinamide bearing a five-methylene linkage not only inherited the excellent substrate generality from the monosulfinamide catalysts, but also exhibited further improved enantioselectivity.

Enantioselective hydrosilylation of ketimines catalyzed by Lewis basic C2-symmetric chiral tetraamide

l-Proline derived C2-symmetric chiral tetraamide 5b was found to behave as an effective Lewis basic catalyst in the enantioselective hydrosilylation of ketimines, affording high isolated yields (up to 95%) and moderate to high enantioselectivit

S-chiral sulfinamides as highly enantioselective organocatalysts

(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

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

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

Asymmetric reductions of imines and ketones by chiral oxaborolidines

Asymmetric reduction of imines were studied using dialkoxyborane 1. Dihydro-β-carboline 5a showed moderate (42% ee) and N-phenylketimine 10 higher enantioselectivity (73% ee). Asymmetric reduction of ketones with oxazaborolidine 33 showed high enantioselectivities.

Asymmetric reduction of imines with chiral dialkoxyboranes

The asymmetric reduction of imines with chiral dialkoxyboranes was investigated and gave an optically active amine up to 73%ee in the presence of MgBr2·OEt2.

Enantioselective synthesis of optically active secondary amines via asymmetric reduction

The enantioselective synthesis of optically active secondary amines via the asymmetric reduction of N-substituted ketimines with various chiral hydride reagents, such as Itsuno's reagent (1), Corey's reagent (2), K glucoride (3), Sharpless' reagent (4), a