Kinetic resolution of racemic 6-substituted 3-methyl-3,4-dihydro-2H-[1,4]benzoxazines with chiral acyl chlorides

被引：0
|
作者：
Chulakov, E. N. [1 ]
Korolyova, M. A. [1 ]
Tumashov, A. A. [1 ]
Kodess, M. I. [1 ]
Levit, G. L. [1 ]
Krasnov, V. P. [1 ]
机构：
[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, 22-20 Ul S Kovalevskoi, Ekaterinburg 620108, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2023年 / 72卷 / 12期
基金：
俄罗斯科学基金会;
关键词：
1,4]benzoxazines; kinetic resolution; racemic amines; acyl chlorides; acylation; selectivity; transition state; density functional theory (DFT); HETEROCYCLIC AMINES; DIASTEREOSELECTIVE ACYLATION; SEPARATION;
D O I：
10.1007/s11172-023-4104-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A comparative study of the kinetic resolution of racemic 6-methoxy-, 6-nitro-, and 6-chloro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines with (S)-naproxen acyl chloride, N-phthaloyl-(S)-leucyl chloride, and O-phenyl-(R)-lactyl chloride was carried out. The selectivity factors in the kinetic resolution of racemic amines with (S)-naproxen acyl chloride and O-phenyl-(R)-lactyl chloride were higher compared to N-phthaloyl-(S)-leucyl chloride. The factors responsible for the stereodifferentiation in the kinetic resolution of racemic dihydrobenzoxazines containing groups with different electronic properties were explained based on DFT calculations. Stacking interactions between aromatic moieties in the transition state were demonstrated to play a key role in the stereodifferentiation.
引用
收藏
页码：2938 / 2947
页数：10
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