144222-34-4Relevant articles and documents
Synthesis of simple enantiopure tetrahydro-β-carbolines and tetrahydroisoquinolines
Tietze, Lutz F.,Zhou, Yifa,Toepken, Enno
, p. 2247 - 2252 (2000)
Enantioselective hydrogenation of the imines 11-13, 27 and 30 with the Ru complex (R,R)-5 led to the tetrahydro-β-carbolines (1S)-14, (1R)-21 and (1S)-22, and the tetrahydroisoquinoline (1S)-31 with ee > 95%. By employing (S,S)-5 the enantiomers are accessible. The imines 11-12 and 27 were obtained by oxidation of racemic 14, 21 and 22 with KMnO4 in > 58% yield.
O-bicyclic amine compounds as well as preparation method and chiral products thereof
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Paragraph 0078; 0148-0149, (2017/11/04)
The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.
(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins
Zhang, Chao,Li, Jing,Tian, Jun,Fang, Wangwang,Li, Yang,Chen, Ligong,Yan, Xilong
supporting information, p. 1248 - 1258 (2015/03/30)
Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.