108535-35-9Relevant academic research and scientific papers
Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts
Ishii, Akihiro,Mikami, Koichi
, p. 51 - 55 (1999)
Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts gave reactive vinyl ether products. Sequential diastereoselective reactions of resultant vinyl ethers with m-CPBA provided highly functionalized organofluorine compounds in high enantiomeric purity.
Practical asymmetric synthesis of β-hydroxy-β-trifluoromethylated ketones via the first example of the in situ generation of trifluoroacetaldehyde and its successive asymmetric carbon-carbon bond formation reaction with chiral imines
Funabiki, Kazumasa,Hashimoto, Wataru,Matsui, Masaki
, p. 2056 - 2057 (2004)
Not only trifluoroactaldehyde ethyl hemiacetal or hydrate but also other polyfluoroalkylaldehydes acetals or hydrates react with an equimolar amount of various chiral imines, followed by hydrolysis to produce the corresponding (S)-β-hydroxy-β-polyfluoroal
Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties
Sperandio, Céline,Rodriguez, Jean,Quintard, Adrien
, p. 1629 - 1635 (2020)
Fluorine is able to confer unique properties to organic molecules but the scarcity of natural organofluorine sources renders the development of new synthetic methods highly desirable. Using a chiral BOX/Cu combination, enantioselective decarboxylative aldolization of perfluorinated aldehydes has been developed. Most notably, the reaction occurring under mild conditions and with high enantiocontrol can create ketodiols in one single synthetic operation, which are precursors of crucial perfluorinated 1,3,5-triols. In addition, the reaction performed with chloral, validates the proposed transition state model based on steric interactions and provides the first enantioselective synthesis of hexachlorinated ketodiol of great synthetic utility. The ability of perfluorinated 1,3,5-triols to form a central hydrogen-bonding framework allows strong coordination of anions and the chirality obtained through the catalyst-controlled synthetic sequence demonstrates the selective chiral anion recognition ability of polyols.
Chiral Bipyridine Ligand with Flexible Molecular Recognition Site: Development and Application to Copper-Catalyzed Asymmetric Borylation of α,β-Unsaturated Ketones
Tsutsumi, Ryosuke,Taguchi, Rika,Yamanaka, Masahiro
, (2021/10/20)
A novel chiral bipyridine ligand bearing a flexible side chain with a molecular recognition site enables precise stereocontrol through the cooperative action of metal center and hydrogen bonds. This new chiral ligand was applied to the copper-catalyzed as
Ru-Catalyzed Chemo- and Enantioselective Hydrogenation of β-Diketones Assisted by the Neighboring Heteroatoms
Li, Wanfang,Lu, Bin,Xie, Xiaomin,Zhang, Zhaoguo
, p. 5509 - 5513 (2019/08/01)
A highly chemo- and enantioselective hydrogenation of β-diketones was achieved by using [Ru(benzene)(S)-SunPhosCl]Cl for consistency in THF. The neighboring heteroatoms played important roles in guaranteeing the reactivity and controlling the chemoselectivity. These results suggested a potential approach for the clean and facile synthesis of functionalized chiral β-hydroxy ketones, which could otherwise be prepared through much less step-economic transformations.
C2-Symmetric Chiral Bisoxazolines as Hydrogen-Bond-Acceptor Catalysts in Enantioselective Aldol Reaction of β-Carbonyl Acids with Trifluoroacetaldehyde Hemiacetals
Yang, Zhen-Yan,Zeng, Jun-Liang,Ren, Nan,Meng, Wei,Nie, Jing,Ma, Jun-An
supporting information, p. 6364 - 6367 (2016/12/23)
A simple C2-symmetric chiral bisoxazoline is demonstrated to use hydrogen bonding to catalyze an important family of aldol reactions of trifluoroacetaldehyde hemiacetals with various β-carbonyl acids. This reaction is highly enantioselective, delivering chiral nonracemic trifluoromethylated alcohols with excellent optical purity and good isolated yields. This concept of relaying chiral information via a chiral hydrogen-bond acceptor should be applicable to a vast number of organocatalytic processes.
Asymmetric chemoenzymatic synthesis of 1,3-diols and 2,4-disubstituted aryloxetanes by using whole cell biocatalysts
Vitale, Paola,Perna, Filippo Maria,Agrimi, Gennaro,Scilimati, Antonio,Salomone, Antonio,Cardellicchio, Cosimo,Capriati, Vito
, p. 11438 - 11445 (2016/12/16)
Regio- and stereo-selective reduction of substituted 1,3-aryldiketones, investigated in the presence of different whole cell microorganisms, was found to afford β-hydroxyketones or 1,3-diols in very good yields (up to 95%) and enantiomeric excesses (up to 96%). The enantiomerically enriched aldols, obtained with the opposite stereo-preference by baker's yeast and Lactobacillus reuteri DSM 20016 bioreduction, could then be diastereoselectively transformed into optically active syn- or anti-1,3-diols by a careful choice of the chemical reducing agent (diastereomeric ratio up to 98 : 2). The latter, in turn, were stereospecifically cyclized into the corresponding oxetanes in 43-98% yields and in up to 94% ee, thereby giving a diverse selection of stereo-defined 2,4-disubstituted aryloxetanes.
Copper-catalyzed one-pot denitrogenative-dehydrogenative-decarboxylative coupling of β-ketoacids with trifluorodiazoethane: Facile access to trifluoromethylated aldol products
Xiong, Heng-Ying,Yang, Zhen-Yan,Chen, Zhen,Zeng, Jun-Liang,Nie, Jing,Ma, Jun-An
supporting information, p. 8325 - 8329 (2014/07/08)
A novel copper-catalyzed one-pot cross-coupling of β-ketoacids with in situ generated trifluorodiazoethane has been developed. This reaction provides a direct and efficient method, in which one C-C bond and one C-O bond were formed in a carbenoid center with concomitant denitrogenation-dehydrogenation- decarboxylation, to afford trifluoromethylated aldol products. In several preliminary experiments, good to high enantioselectivities were also obtained.
Discovery of 4-Aryl-7-hydroxyindoline-based P2Y1 antagonists as novel antiplatelet agents
Yang, Wu,Wang, Yufeng,Lai, Amy,Qiao, Jennifer X.,Wang, Tammy C.,Hua, Ji,Price, Laura A.,Shen, Hong,Chen, Xue-Qing,Wong, Pancras,Crain, Earl,Watson, Carol,Huang, Christine S.,Seiffert, Dietmar A.,Rehfuss, Robert,Wexler, Ruth R.,Lam, Patrick Y. S.
, p. 6150 - 6164 (2014/08/18)
Adenosine diphosphate (ADP)-mediated platelet aggregation is signaled through two distinct G protein-coupled receptors (GPCR) on the platelet surface: P2Y12 and P2Y1. Blocking P2Y12 receptor is a clinically well-validated strategy for antithrombotic therapy. P2Y1 antagonists have been shown to have the potential to provide equivalent antithrombotic efficacy as P2Y12 inhibitors with reduced bleeding in preclinical animal models. We have previously reported the discovery of a potent and orally bioavailable P2Y1 antagonist, 1. This paper describes further optimization of 1 by introducing 4-aryl groups at the hydroxylindoline in two series. In the neutral series, 10q was identified with excellent potency and desirable pharmacokinetic (PK) profile. It also demonstrated similar antithrombotic efficacy with less bleeding compared with the known P2Y 12 antagonist prasugrel in rabbit efficacy/bleeding models. In the basic series, 20c (BMS-884775) was discovered with an improved PK and liability profile over 1. These results support P2Y1 antagonism as a promising new antiplatelet target.
Chiral bifunctional thiourea-catalyzed enantioselective aldol reaction of trifluoroacetaldehyde hemiacetal with aromatic ketones
Nie, Jing,Li, Xiao-Juan,Zheng, Dong-Hua,Zhang, Fa-Guang,Cui, Shumin,Ma, Jun-An
experimental part, p. 468 - 473 (2011/08/07)
In the presence of saccharide-derived bifunctional amine-thiourea catalysts, the direct aldol condensation of trifluoroacetaldehyde methyl hemiacetal with aromatic ketones proceeds to produce (R)-β-hydroxy β-trifluoroalkyl ketones in low to moderate yield
