Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride

Vakarov, Sergey А.; Gruzdev, Dmitry А.; Chulakov, Evgeny N.; Садретдинова, Л. Ш.; Тумашов, А. А.; Первова, М. Г.; Ежикова, М. А.; Кодесс, М. И.; Левит, Г. Л.; Краснов, В. П.; Charushin, Valery N.

doi:10.1016/j.tetasy.2016.10.004

Cited by 14 publications

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References 31 publications

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“…KR of racemic acyl chlorides 3 a,b,d,f under the action of enantiopure ( S )‐amines 1 a and 1 b (99 % ee ) was carried out according to the method we used to assign the configuration of the synthesized amides (see Scheme ), except that the acylation was carried out at −20 °C, since lowering the reaction temperature, as we showed earlier,– leads to better stereochemical results. For KR of racemic acyl chlorides 3 a and 3 b , we used fluorinated amine ( S )‐ 1 b ; for KR of compounds 3 d and 3 f , benzoxazine ( S )‐ 1 a (Scheme , Table ).…”

Section: Resultsmentioning

confidence: 99%

Kinetic Resolution of Racemic 2‐Aryloxy Propionyl Chlorides Using Enantiopure (S)‐3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines

et al. 2020

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Stereoselectivity in the mutual kinetic resolution (KR) of racemic 3,4-dihydro-3-methyl-2H- [1,4]benzoxazines and racemic 2-aryloxy propionyl chlorides was studied. Based on the results obtained, preparative methods for single enantiomers of a series of 2-aryloxy propionic acids via acylative KR of their racemates with enantiopure (S)-3,4-dihydro-3-methyl-2H- [1,4] benzoxazines have been proposed.

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Section: Resultsmentioning

confidence: 99%

Kinetic Resolution of Racemic 2‐Aryloxy Propionyl Chlorides Using Enantiopure (S)‐3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines

et al. 2020

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Mutual Kinetic Resolution of Racemic 3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines with Acyl Chlorides of Racemic O‐Phenyllactic Acids and DFT Modelling of Transition States

et al. 2018

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The effect of the electronic nature of the para substituent on the aromatic ring of 2‐aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4‐dihydro‐3‐methyl‐2H‐[1,4]benzoxazine and its 7,8‐difluoro‐containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO‐CH2Cl2‐B3LYP‐D3‐gCP/def2‐TZVP (or def2‐SVP)//B3LYP‐D3‐gCP/def2‐SVP level of theory. It has been found that a low‐cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2‐aryloxyacyl chlorides.

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N‐[ω‐(Purin‐6‐yl)aminoalkanoyl] Derivatives of Chiral Heterocyclic Amines as Promising Anti‐Herpesvirus Agents

et al. 2019

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Novel conjugates of 2‐aminopurine and purine containing fragments of chiral heterocyclic amines attached at position 6 of purine core via a linker, fragment of omega‐amino acid, have been synthesized and evaluated in vitro for their anti‐herpetic activity in the Vero E6 cells; as a result, a new group of compounds possessing high inhibitory activity against herpes simplex virus type 1, including acyclovir‐resistant (TK–) strain has been revealed. The anti‐herpetic activity of the synthesized compounds is substantially dependent on the stereo configuration of the fragment of heterocyclic amine.

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Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride

Cited by 14 publications

References 31 publications

Kinetic Resolution of Racemic 2‐Aryloxy Propionyl Chlorides Using Enantiopure (S)‐3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines

Kinetic Resolution of Racemic 2‐Aryloxy Propionyl Chlorides Using Enantiopure (S)‐3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines

Mutual Kinetic Resolution of Racemic 3,4‐Dihydro‐3‐methyl‐2H‐[1,4]benzoxazines with Acyl Chlorides of Racemic O‐Phenyllactic Acids and DFT Modelling of Transition States

N‐[ω‐(Purin‐6‐yl)aminoalkanoyl] Derivatives of Chiral Heterocyclic Amines as Promising Anti‐Herpesvirus Agents

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