127733-39-5Relevant articles and documents
Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases
Martínez-Montero, Lía,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
, p. 474 - 480 (2017/06/23)
A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero) aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90-99% ee) and conversion values (67-99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.
PYRIMIDINEDIONE COMPOUNDS AGAINST CARDIAC CONDITIONS
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, (2015/01/07)
Provided are novel pyrimidine dione compounds and pharmaceutically acceptable salts thereof, that are useful for the treatment of hypertrophic cardiomyopathy (HCM) and conditions associated with left ventricular hypertrophy or diastolic dysfunction. The synthesis and characterization of the compounds and pharmaceutically acceptable salts thereof, are described, as well as methods for treating HCM and other forms of heart disease.
Step-efficient access to chiral primary amines
Nugent, Thomas C.,Marinova, Sofiya M.
, p. 153 - 166 (2013/02/25)
Routes to enantioenriched amines are outlined that employ reductive amination and carbanion addition methods. The strategies require either one or two reaction steps from prochiral carbonyl compounds for the synthesis of the corresponding chiral primary amines. Georg Thieme Verlag Stuttgart New York.
Sequential reductive amination-hydrogenolysis: A one-pot synthesis of challenging chiral primary amines
Nugent, Thomas C.,Negru, Daniela E.,El-Shazly, Mohamed,Hu, Dan,Sadiq, Abdul,Bibi, Ahtaram,Umar, M. Naveed
supporting information; experimental part, p. 2085 - 2092 (2011/10/19)
Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxyphenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions. Copyright
Highly regioselective hydrogenolysis of bis(α-methylbenzyl)amine derivatives affected by the trifluoromethyl substituent on the aromatic ring
Kanai, Masatomi,Yasumoto, Manabu,Kuriyama, Yokusu,Inomiya, Kenjin,Katsuhara, Yutaka,Higashiyama, Kimio,Ishii, Akihiro
, p. 1007 - 1010 (2007/10/03)
(Matrix presented) The highly regioselective hydrogenolysis of bis(α-methylbenzyl)amine derivatives proceeded with influence not from the electronic effect but from the steric effect of the trifluoromethyl substituent on the aromatic ring to provide a practical asymmetric synthesis of trifluoromethyl-substituted α-phenylethylamines.
Optically active amines. 34.1 Application of the benzene chirality rule to ring-substituted phenylcarbinamines and carbinols
Pickard, Simeon T.,Smith, Howard E.
, p. 5741 - 5747 (2007/10/02)
The negative sign of the 1Lb, Cotton effects (CEs) from about 250 to 270 nm in the circular dichroism (CD) spectra of (R)-α-phenylethylamine and (R)-α-phenylethyl alcohol and other phenylalkylcarbinamines and carbinols is determined by vibronic borrowing from allowed transitions at shorter wavelength. On ring substitution, bond transition moments are induced in the benzene ring bonds adjacent to the attachment bond of the chiral group, resulting in enhanced coupling of the 1Lb transition with the chiral group. A sign reversal for the 1Lb, CEs on para substitution with an atom or group with a positive spectroscopic moment (C1, CH3) can be viewed as the overshadowing of the vibronic contribution by an induced contribution of opposite sign On para substitution with a group with a negative spectroscopic moment (CF3, CN), the sign of the 1Lb CEs is unchanged since the vibronic and induced contributions have the same sign. Meta substitution by an atom or group will result in bond moments in an opposite sense from that caused by the same atom or group in the para position. Thus on meta substitution by a group with a positive spectroscopic moment (C1, CH3), both the vibronic and induced contributions have the same sign, and the sign of the 1Lb CEs is the same as that of the unsubstituted parent. For meta substitution by a group with a negative spectroscopic moment (CF3, CN), the sign of the induced contribution is opposite to that of the vibronic contribution. In the case of CF3 and CN groups, the latter is more important than the former, and the sign of the 1Lb CEs is the same as that of the unsubstituted parent. Ortho substitution again reverses the sense of the induced bond transition moments from that induced by the same meta substituents. Thus, provided the position of the substituent and its spectroscopic moment are taken into account the absolute configuration of substituted phenylmethylcarbinamines and carbinols can often be assigned.
