63209-58-5Relevant academic research and scientific papers
Chiral Br?nsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane
Skrypai, Vladislav,Varjosaari, Sami E.,Azam, Fawwaz,Gilbert, Thomas M.,Adler, Marc J.
, p. 5021 - 5026 (2019/05/10)
The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Br?nsted acid catalyst is reported. This is the first known example of chiral Br?nsted acid-catalyzed asymmetric reductive amination using
Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines
Xing, Yongfei,Wu, Shijie,Dong, Mengxian,Wang, Jie,Liu, Li,Zhu, Huajie
supporting information, (2019/08/08)
A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.
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
Asymmetric hydrogenation of imines with chiral alkene-derived boron Lewis acids
Liu, Xiaoqin,Liu, Ting,Meng, Wei,Du, Haifeng
supporting information, p. 8686 - 8689 (2018/11/30)
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
NOVEL PICOLINAMIDE-CINCHONA ORGANOCATALYSTS AND DERIVATIVES
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Paragraph 0058, (2016/09/12)
The present application describes a novel type of picolinamide-cinchona organocatalyst that allows for the successful transformation of ketimines to chiral amines with very high enantioselectivities and with the highest TOFs reported for any particular organocatalyst to date. These organocatalysts have also been immobilized to a variety of solid supports, including magneto-nanoparticles.
Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation
Barrulas, Pedro C.,Genoni, Andrea,Benaglia, Maurizio,Burke, Anthony J.
, p. 7339 - 7342 (2016/02/20)
Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosi
Novel carbohydrate-derived pyridinecarboxylic organocatalysts for the enantioselective reduction of imines with trichlorosilane
Ge, Xin,Qian, Chao,Chen, Yunbin,Chen, Xinzhi
, p. 596 - 601 (2014/05/20)
A new type of carbohydrate-derived pyridinecarboxylic organocatalyst was prepared by fine-tuning a d-glucosamine backbone at the C-2 and C-3 positions. The carbohydrate-derived pyridinecarboxylic organocatalyst was used for the enantioselective reduction of imines with trichlorosilane. The reduction proceeded in high yield (up to 93%) and with moderate enantioselectivity (up to 75%).
Chiral phosphoric-acid-catalyzed transfer hydrogenation of ethyl ketimine derivatives by using benzothiazoline
Saito, Kodai,Horiguchi, Kosaku,Shibata, Yukihiro,Yamanaka, Masahiro,Akiyama, Takahiko
, p. 7616 - 7620 (2014/07/07)
Chiral phosphoric acid catalyzed transfer hydrogenation of ketimines derived from propiophenone derivatives and reductive amination of alkyl ethyl ketone derivatives were extensively examined in the presence of two representative hydrogen donors. The exce
Synthesis of novel carbohydrate-based valine-derived formamide organocatalysts by CuAAC click chemistry and their application in asymmetric reduction of imines with trichlorosilane
Ge, Xin,Qian, Chao,Chen, Xinzhi
, p. 1450 - 1455 (2015/01/08)
Novel organocatalysts combining carbohydrate and N-formyl-l-valine derivatives were prepared by CuII-catalyzed diazo transfer and CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition CuAAC click chemistry. It was found that the carbohydrate-based valine-derived formamide organocatalyst had high catalytic activity for the asymmetric reduction of imines with trichlorosilane. The reduction can proceed at room temperature in toluene in high yield (up to 98%) and with excellent enantioselectivity (up to 94%). 'CuAAC' click chemistry is a bridge to link N-formyl-l-valine derived organocatalysts with carbohydrates.
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
Wang, Zhouyu,Wang, Chao,Zhou, Li,Sun, Jian
, p. 787 - 797 (2013/02/25)
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.
