83829-03-2Relevant articles and documents
Amino alcohols using the optically active amino alcohol derivative bi- Nord complex boron - -
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Paragraph 0064; 0071-0076; 0232-0234; 0236-0238, (2021/04/16)
Disclosed are an amino alcohol-boron-binol complex as an intermediate, including Complex 3-1-1 shown below, and a method for preparing an optically active amino alcohol by using the same, wherein a racemic amino alcohol is resolved in an enationselective manner using a boron compound and a (R)- or (S)-binol, whereby an amino alcohol derivative with high optical purity can be prepared at high yield.
Synthesis method of beta-amino alcohol compounds
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Paragraph 0134-0141, (2020/03/29)
The invention discloses a synthesis method of beta-amino alcohol compounds. A carboxylic acid is adopted as a catalyst to promote amination of an epoxide to generate the beta-amino alcohol compounds.Compared with reported methods, this method has advantages of no use of metal catalysts, mild reaction conditions, the safe, non-toxic, cheap and readily available catalyst, a high product yield and high regioselectivity. In addition, a low-boiling-point carboxylic acid can be selected as the catalyst. When the low-boiling-point catalyst is used, excess raw materials and the catalyst can be recycled and reused, almost no waste is discharged to the environment, a post-treatment process does not require extraction, drying, filtration or the like, and a mixture after the reaction is finished is simply distilled or distilled under reduced pressure to obtain a crude product with higher purity. The synthesis process is simple, efficient, and environmentally friendly.
Highly regioselective ring-opening of epoxides with amines: A metal- A nd solvent-free protocol for the synthesis of β-amino alcohols
Li, Dong,Wang, Jing,Yu, Shibo,Ye, Silei,Zou, Wenjie,Zhang, Hongbin,Chen, Jingbo
supporting information, p. 2256 - 2259 (2020/03/04)
We herein report a metal- A nd solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines. This process provides β-amino alcohols in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol can be used for the introduction of amines in natural products during late-stage transformations.
Photoinduced Olefin Diamination with Alkylamines
Angelini, Lucrezia,Govaerts, Sebastian,Hampton, Charlotte,Leonori, Daniele,Malet-Sanz, Laia,Ruffoni, Alessandro
supporting information, p. 15021 - 15028 (2020/06/17)
Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.
In Situ Conformational Fixation of the Amide Bond Enables General Access to Medium-Sized Lactams via Ring-Closing Metathesis
Hegmann, Nina,Prusko, Lea,Diesendorf, Nina,Heinrich, Markus R.
supporting information, p. 7825 - 7829 (2019/01/04)
In this work, a novel phenethylamine-derived protecting group is introduced, which is able to significantly enhance the Grubbs I-catalyzed formation of 9- to 12-membered lactams through charge-induced conformational fixation under acidic conditions. As the new approach is particularly valuable for 10- and 11-membered ring systems, for which no related precedence was available so far, the overall strategy now offers general access to medium-sized lactams via ring closing metathesis. Cleavage of the protecting group can be achieved through a mild sequence combining N-oxidation and Cope elimination or alternatively under standard hydrogenation conditions.
Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
Acocella, Maria Rosaria,D'Urso, Luciana,Maggio, Mario,Guerra, Gaetano
, p. 1915 - 1920 (2016/07/06)
The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solvent-free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by π-stacking interactions with the graphitic π system. The described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency. Moreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxides and provide chiral β-amino alcohols with enantiomeric excess values up to 99 %.
Versatile iridicycle catalysts for highly efficient and chemoselective transfer hydrogenation of carbonyl compounds in water
Talwar, Dinesh,Wu, Xiaofeng,Saidi, Ourida,Salguero, Noemí Poyatos,Xiao, Jianliang
supporting information, p. 12835 - 12842 (2015/03/30)
Cyclometalated iridium complexes are shown to be highly efficient and chemoselective catalysts for the transfer hydrogenation of a wide range of carbonyl groups with formic acid in water. Examples include α-substituted ketones (α-ether, α-halo, α-hydroxy, α-amino, α-nitrile or α-ester), α-keto esters, β-keto esters and α,β-unsaturated aldehydes. The reduction was carried out at substrate/catalyst ratios of up to 50000 at pH 4.5 and required no organic solvent. The protocol provides a practical, easy and efficient way for the synthesis of β-functionalised secondary alcohols, such as β-hydroxyethers, β-hydroxyamines and β-hydroxyhalo compounds, which are valuable intermediates in pharmaceutical, fine chemical, perfume and agrochemical synthesis. Water wonder: Iridicycle catalysts are versatile and allow the highly efficient and chemoselective transfer hydrogenation of a variety of carbonyl compounds, including problematic and challenging ones, with formate in neat water (see scheme).
Magnetic nano Fe3O4 catalyzed solvent-free stereo- and regioselective a-aminolysis of epoxides by amines; A green method for the synthesis of β-amino alcohols
Kumar, Amit,Parella, Ramarao,Babu, Srinivasarao Arulananda
, p. 835 - 842 (2014/04/17)
We report the use of magnetic nano Fe3O4 as a mild heterogeneous catalyst for the aminolysis of epoxides with amines. The approach constitutes a green method for the formation of a variety of β-amino alcohols with very high stereo- and regioselectivity under solvent-free and ambient reaction conditions. The aminolysis of chiral epoxides with amines gave the corresponding chiral β-amino alcohols with complete inversion of stereochemistry. The magnetic nano Fe3O4 catalyst can be easily recovered and recycled. Georg Thieme Verlag Stuttgart New York.
Metal free chemoselective reduction of α-keto amides using TBAF as catalyst
Mamillapalli, N. Chary,Sekar, Govindasamy
, p. 61077 - 61085 (2015/02/19)
The metal and ligand free chemoselective reduction of the keto group and complete reduction of the both keto and amide groups of α-keto amide with hydrosilanes using tetrabutylammoniumflouride (TBAF) as catalyst have been accomplished. This methodology affords an efficient and economic route for the synthesis of biologically important α-hydroxy amides and β-amino alcohols. The other important advantage of this TBAF catalyst is chemoselective reduction of ketones to corresponding alcohols in the presence of several other sensitive functional groups.
An efficient protocol for regioselective ring opening of epoxides using sulfated tungstate: Application in synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine
Pathare, Sagar P.,Akamanchi, Krishnacharya G.
supporting information, p. 6455 - 6459 (2013/11/19)
Sulfated tungstate was found to be a new and highly efficient catalyst for opening of epoxide rings by amines to give β-amino alcohols with high regioselectivity. Various advantages associated with this novel and environmental friendly protocol include solvent-free conditions, short reaction times, high product yields, simple workup procedure and easy recovery and reusability of the catalyst. This protocol has been applied for the synthesis of active pharmaceutical ingredients atenolol, propranolol and ranolazine.
