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Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline

Victor Pavlovich Krasnov 1
Victor Pavlovich Krasnov
, 
Galina L'vovna Levit 1
Galina L'vovna Levit
, 
Irina Nikolaevna Andreeva 1
Irina Nikolaevna Andreeva
, 
Alexander Nikolaevich Grishakov 1
Alexander Nikolaevich Grishakov
,  , 
Oleg Nikolaevich Chupakhin 1
Oleg Nikolaevich Chupakhin
10.1070/MC2002v012n01ABEH001545
Published 2002-03-11
Communication , Volume 12, Issue 1, 27-28
33
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Krasnov V. P. et al. Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline // Mendeleev Communications. 2002. Vol. 12. No. 1. pp. 27-28.
GOST all authors (up to 50) Copy
Krasnov V. P., Levit G. L., Andreeva I. N., Grishakov A. N., Charushin V. N., Chupakhin O. N. Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline // Mendeleev Communications. 2002. Vol. 12. No. 1. pp. 27-28.
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TY - JOUR
DO - 10.1070/MC2002v012n01ABEH001545
UR - https://mendcomm.colab.ws/publications/10.1070/MC2002v012n01ABEH001545
TI - Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline
T2 - Mendeleev Communications
AU - Krasnov, Victor Pavlovich
AU - Levit, Galina L'vovna
AU - Andreeva, Irina Nikolaevna
AU - Grishakov, Alexander Nikolaevich
AU - Charushin, Valery Nikolaevich
AU - Chupakhin, Oleg Nikolaevich
PY - 2002
DA - 2002/03/11
PB - Mendeleev Communications
SP - 27-28
IS - 1
VL - 12
ER -
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@article{2002_Krasnov,
author = {Victor Pavlovich Krasnov and Galina L'vovna Levit and Irina Nikolaevna Andreeva and Alexander Nikolaevich Grishakov and Valery Nikolaevich Charushin and Oleg Nikolaevich Chupakhin},
title = {Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline},
journal = {Mendeleev Communications},
year = {2002},
volume = {12},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2002v012n01ABEH001545},
number = {1},
pages = {27--28},
doi = {10.1070/MC2002v012n01ABEH001545}
}
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Krasnov, Victor Pavlovich, et al. “Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline.” Mendeleev Communications, vol. 12, no. 1, Mar. 2002, pp. 27-28. https://mendcomm.colab.ws/publications/10.1070/MC2002v012n01ABEH001545.

Abstract

The acylation of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline by (S)-naproxen acyl chloride resulted in their kinetic resolution with the predominant formation of (S,S)-diastereoisomeric amides (de 78–76%), recrystallisation of which followed by acid hydrolysis gave individual (S)-isomers of heterocyclic amines.

References

1.
Stereoselective Organic Synthesis via Dynamic Kinetic Resolution
Noyori R., Tokunaga M., Kitamura M.
Bulletin of the Chemical Society of Japan, 1995
2.
Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazines with (S)-naproxen
Charushin V.N., Krasnov V.P., Levit G.L., Korolyova M.A., Kodess M.I., Chupakhin O.N., Kim M.H., Lee H.S., Park Y.J., Kim K.
Tetrahedron Asymmetry, 1999