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Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate

Yurii Nikolaevich Belokon 1
Yurii Nikolaevich Belokon
, 
Konstantin Aleksandrovich Kochetkov 1
Konstantin Aleksandrovich Kochetkov
, 
Tat'yana Dmitrievna Churkina 1
Tat'yana Dmitrievna Churkina
, 
Nikolai Sergeyevich Ikonnikov 1
Nikolai Sergeyevich Ikonnikov
, 
Svetlana A Orlova 1
Svetlana A Orlova
, 
Valeriy Valentinovich Smirnov 2
Valeriy Valentinovich Smirnov
, 
Alexey Anatol'evich Chesnokov 2
Alexey Anatol'evich Chesnokov
10.1070/MC1997v007n04ABEH000790
Published 1997-08-30
Communication , Volume 7, Issue 4, 137-138
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Belokon Y. N. et al. Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate // Mendeleev Communications. 1997. Vol. 7. No. 4. pp. 137-138.
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Belokon Y. N., Kochetkov K. A., Churkina T. D., Ikonnikov N. S., Orlova S. A., Smirnov V. V., Chesnokov A. A. Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate // Mendeleev Communications. 1997. Vol. 7. No. 4. pp. 137-138.
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TY - JOUR
DO - 10.1070/MC1997v007n04ABEH000790
UR - https://mendcomm.colab.ws/publications/10.1070/MC1997v007n04ABEH000790
TI - Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate
T2 - Mendeleev Communications
AU - Belokon, Yurii Nikolaevich
AU - Kochetkov, Konstantin Aleksandrovich
AU - Churkina, Tat'yana Dmitrievna
AU - Ikonnikov, Nikolai Sergeyevich
AU - Orlova, Svetlana A
AU - Smirnov, Valeriy Valentinovich
AU - Chesnokov, Alexey Anatol'evich
PY - 1997
DA - 1997/08/30
PB - Mendeleev Communications
SP - 137-138
IS - 4
VL - 7
ER -
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@article{1997_Belokon,
author = {Yurii Nikolaevich Belokon and Konstantin Aleksandrovich Kochetkov and Tat'yana Dmitrievna Churkina and Nikolai Sergeyevich Ikonnikov and Svetlana A Orlova and Valeriy Valentinovich Smirnov and Alexey Anatol'evich Chesnokov},
title = {Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate},
journal = {Mendeleev Communications},
year = {1997},
volume = {7},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1997v007n04ABEH000790},
number = {4},
pages = {137--138},
doi = {10.1070/MC1997v007n04ABEH000790}
}
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Belokon, Yurii Nikolaevich, et al. “Asymmetric Michael addition of a glycine synthon to methyl methacrylate, mediated by disodium TADDOLate.” Mendeleev Communications, vol. 7, no. 4, Aug. 1997, pp. 137-138. https://mendcomm.colab.ws/publications/10.1070/MC1997v007n04ABEH000790.

Abstract

The disodium salt of (4R,5R)-(TADDOL), 3, can be used as a mediator in the asymmetric Michael reaction, e.g. 1,4-addition of a glycine synthon 1 to methyl methacrylate 2, mediated by 3 (10–100 mol%), gives a diastereoisomeric excess of the corresponding product 4 up to 65% and an enantiomeric purity ca. 28%; (2S,4R)-4-methylglutamic acid (ee ≥ 85%), 6, was obtained starting from (2S,4R)-4 (ee 28%) through the recrystallization and decomposition of the latter.

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