189619-55-4Relevant articles and documents
Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids
Zhu, Chendan,Mandrelli, Francesca,Zhou, Hui,Maji, Rajat,List, Benjamin
, p. 3312 - 3317 (2021/04/07)
We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.
Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
Seo, Hyowon,Liu, Aofei,Jamison, Timothy F.
, p. 13969 - 13972 (2017/10/17)
The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.
Beta amino acid-modified and fluorescently labelled kisspeptin analogues with potent KISS1R activity
Camerino,Liu,Moriya,Kitahashi,Mahgoub,Mountford,Chalmers,Soga,Parhar,Thompson
, p. 406 - 414 (2016/08/28)
Kisspeptin analogues with improved metabolic stability may represent important ligands in the study of the kisspeptin/KISS1R system and have therapeutic potential. In this paper we assess the activity of known and novel kisspeptin analogues utilising a du
Aminomethylation of enals through carbene and acid cooperative catalysis: Concise access to β2-amino acids
Xu, Jianfeng,Chen, Xingkuan,Wang, Ming,Zheng, Pengcheng,Song, Bao-An,Chi, Yonggui Robin
supporting information, p. 5161 - 5165 (2015/04/27)
A convergent, organocatalytic asymmetric aminomethylation of α,β-unsaturated aldehydes by N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperative catalysis is disclosed. The catalytically generated conjugated acid from the base plays dual roles in promoting the formation of azolium enolate intermediate, formaldehyde-derived iminium ion (as an electrophilic reactant), and methanol (as a nucleophilic reactant). This redox-neutral strategy is suitable for the scalable synthesis of enantiomerically enriched β2-amino acids bearing various substituents. Harmonious cooperation: An N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperatively catalyze the aminomethylation of α,β-unsaturated aldehydes. This cooperative catalytic reaction provides a redox neutral strategy for quick access to β2-amino esters in an enantioselective manner.
Organocatalysed decarboxylative protonation process from Meldrum's acid: Enantioselective synthesis of isoxazolidinones
Tite, Tony,Sabbah, Mohamad,Levacher, Vincent,Briere, Jean-Francois
, p. 11569 - 11571 (2013/12/04)
An asymmetric organocatalysed decarboxylative protonation reaction allowed a straightforward synthesis of α-substituted isoxazolidin-5-ones from readily available 5-substituted Meldrum's acids. This process is initiated by an anionic formal (3+2) cycloaddition-fragmentation, generated in-situ from a sulfone-amide precursor which also served as a latent source of proton.
Synthesis of chiral β2-amino acids by asymmetric hydrogenation
Luehr, Susan,Holz, Jens,Zayas, Odalys,Wendisch, Volkmar,Boerner, Armin
, p. 1301 - 1319 (2012/11/07)
The synthesis of chiral β2-amino acids by homogeneous asymmetric hydrogenation is discussed. Prochiral β-aryl- or β-hetaryl-α-N-benzyl/N-acetyl/N-Boc substituted α- aminomethylacrylates used as substrates were prepared by a Baylis-Hillman react
SEVEN-MEMBERED RING COMPOUND, PRODUCTION METHOD THEREOF AND PHARMACEUTICAL USE THEREOF
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Page/Page column 104, (2009/03/07)
A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.
Highly diastereoselective synthetic route to enantiopure β2-amino acids and γ-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary
Tessier, Arnaud,Lahmar, Nour,Pytkowicz, Julien,Brigaud, Thierry
, p. 3970 - 3973 (2008/09/20)
(Chemical Equation Presented) The alkylation reactions of an amide enolate derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur with a complete diastereoselectivity and in good yields with various electrophiles. This reaction provid
Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith
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Page/Page column 56, (2008/12/07)
Provided herein are Heterocyclic Compounds having the following structure: wherein R1, R2, X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.
INHIBITORS OF AKT ACTIVITY
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Page/Page column 44, (2008/12/04)
Invented are novel pyrazole compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.
