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Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols

Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
, 
Olga Arkadyevna Banina 2
Olga Arkadyevna Banina
, 
Denis Vladimirovich Sudarikov 2
Denis Vladimirovich Sudarikov
, 
Albert Gabidullinovich Nigmatov 1
Albert Gabidullinovich Nigmatov
, 
Larisa Leonidovna Frolova 2
Larisa Leonidovna Frolova
, 
10.1016/j.mencom.2020.03.005
Published 2020-03-02
Communication , Volume 30, Issue 2, 147-149
8
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Zlotin S. G. et al. Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 147-149.
GOST all authors (up to 50) Copy
Zlotin S. G., Banina O. A., Sudarikov D. V., Nigmatov A. G., Frolova L. L., Kutchin A. V. Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 147-149.
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TY - JOUR
DO - 10.1016/j.mencom.2020.03.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.005
TI - Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols
T2 - Mendeleev Communications
AU - Zlotin, Sergei Grigorievich
AU - Banina, Olga Arkadyevna
AU - Sudarikov, Denis Vladimirovich
AU - Nigmatov, Albert Gabidullinovich
AU - Frolova, Larisa Leonidovna
AU - Kutchin, Aleksandr Vasilevich
PY - 2020
DA - 2020/03/02
PB - Mendeleev Communications
SP - 147-149
IS - 2
VL - 30
ER -
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@article{2020_Zlotin,
author = {Sergei Grigorievich Zlotin and Olga Arkadyevna Banina and Denis Vladimirovich Sudarikov and Albert Gabidullinovich Nigmatov and Larisa Leonidovna Frolova and Aleksandr Vasilevich Kutchin},
title = {Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.005},
number = {2},
pages = {147--149},
doi = {10.1016/j.mencom.2020.03.005}
}
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Zlotin, Sergei Grigorievich, et al. “Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols.” Mendeleev Communications, vol. 30, no. 2, Mar. 2020, pp. 147-149. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.005.

Keywords

3-carene
4,6-dibromoisatin
aldol reaction
convolutamydine A
isatin
α-pinene
β-amino alcohols

Abstract

Asymmetric aldol reactions of isatin and 4,6-dibromoisatin with acetone are efficiently catalyzed by β-amino alcohols derived from α-pinene and 3-carene. The target compounds can be isolated by crystallization from toluene, which eliminates the need for using chromatography and makes the asymmetric synthesis of (R)-convolutamydine A (up to 94% ee and yield 75%) simple and convenient.

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