2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines

Chulakov, Evgeny N.; Gruzdev, Dmitry А.; Левит, Г. Л.; Садретдинова, Л. Ш.; Краснов, В. П.; Charushin, Valery N.

doi:10.1007/s11172-011-0149-0

Cited by 18 publications

(2 citation statements)

References 31 publications

(14 reference statements)

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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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“…In recent years we have studied the acylative KR of racemic heterocyclic amines with enantiopure acyl chlorides, the derivatives of amino acids and 2‐arylpropionic and 2‐phenoxy acids . One of the goals of these studies was to establish the dependence of the stereochemical outcome of acylation on the reagent structures and reaction conditions in order to improve the efficiency of KR.…”

Section: Introductionmentioning

confidence: 99%

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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Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds

2011

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Acylative kinetic resolution of racemic amines occupies a highly important place among the methods for preparation of enantio enriched or pure amines. Nonenzymatic acylative kinetic resolution is usually carried out in the presence of chiral acyl‐transfer catalysts or under the action of chiral enantio‐ or diastereoselective resolving agents. Recently, this line of investigations has been rapidly developed and very interesting results of design and synthetic application of both new catalysts and chiral acylating agents have been obtained. This microreview summarizes the recent advances in this area.

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2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines

Cited by 18 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

Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds

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