Home / Publications / Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium

Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium

Olga Vasil'evna Turova 1
Olga Vasil'evna Turova
, 
Albert Gabidullinovich Nigmatov 1
Albert Gabidullinovich Nigmatov
, 
Evgeniya Viktorovna Filatova 1
Evgeniya Viktorovna Filatova
, 
Andrei Alexandrovich Vasil'ev 1
Andrei Alexandrovich Vasil'ev
, 
Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
10.1016/j.mencom.2024.09.022
Published 2024-09-09
Communication , Volume 34, Issue 5, 694-697
1
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Turova O. V. et al. Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 694-697.
GOST all authors (up to 50) Copy
Turova O. V., Nigmatov A. G., Filatova E. V., Vasil'ev A. A., Zlotin S. G. Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 694-697.
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TY - JOUR
DO - 10.1016/j.mencom.2024.09.022
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.022
TI - Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium
T2 - Mendeleev Communications
AU - Turova, Olga Vasil'evna
AU - Nigmatov, Albert Gabidullinovich
AU - Filatova, Evgeniya Viktorovna
AU - Vasil'ev, Andrei Alexandrovich
AU - Zlotin, Sergei Grigorievich
PY - 2024
DA - 2024/09/09
PB - Mendeleev Communications
SP - 694-697
IS - 5
VL - 34
ER -
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@article{2024_Turova,
author = {Olga Vasil'evna Turova and Albert Gabidullinovich Nigmatov and Evgeniya Viktorovna Filatova and Andrei Alexandrovich Vasil'ev and Sergei Grigorievich Zlotin},
title = {Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.022},
number = {5},
pages = {694--697},
doi = {10.1016/j.mencom.2024.09.022}
}
MLA
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Turova, Olga Vasil'evna, et al. “Organocatalytic domino formation of (3R,3aS,9bR)-configured 3-aryl-3a-benzamido-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrroles in carbon dioxide medium.” Mendeleev Communications, vol. 34, no. 5, Sep. 2024, pp. 694-697. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.022.

Keywords

1
2-(2-hydroxybenzylideneamino)malonates
3-b]pyrroles
3a
4
4-arylidene-2-phenyloxazol-5(4H)-ones.
9b-tetrahydrochromeno[4
domino reactions
liquid carbon dioxide
organocatalysis
squaramides

Abstract

Asymmetric cycloaddition/intramolecular rearrangement domino reaction of 2-(2-hydroxybenzylideneamino)- malonates with 4-arylidene-2-phenyloxazol-5(4H)-ones can be efficiently carried out in sub- or supercritical carbon dioxide to afford (3R,3aS,9bR)-3-aryl-3a-benzamido-4-oxo-1,3a,4,9b-tetrahydrochromeno[4,3-b]pyrrole-2,2(3H)- dicarboxylates in high yields with up to 99% ee. Excellent stereoinduction is provided in this process by the use of bifunctional hybrid organocatalyst consisting of squaramide (thiourea) and chiral tertiary amine units.

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