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Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps

Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Nadezhda Victorovna Semenova 1
Nadezhda Victorovna Semenova
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Alexander Valentinovich Vashchenko 1
Alexander Valentinovich Vashchenko
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2019.01.004
Published 2018-12-28
Communication , Volume 29, Issue 1, 17-18
3
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Schmidt E. Y. et al. Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 17-18.
GOST all authors (up to 50) Copy
Schmidt E. Y., Semenova N. V., Ushakov I. A., Vashchenko A. V., Trofimov B. A. Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps // Mendeleev Communications. 2018. Vol. 29. No. 1. pp. 17-18.
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TY - JOUR
DO - 10.1016/j.mencom.2019.01.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.004
TI - Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps
T2 - Mendeleev Communications
AU - Schmidt, Elena Yur'evna
AU - Semenova, Nadezhda Victorovna
AU - Ushakov, Igor Alekseevich
AU - Vashchenko, Alexander Valentinovich
AU - Trofimov, Boris Aleksandrovich
PY - 2018
DA - 2018/12/28
PB - Mendeleev Communications
SP - 17-18
IS - 1
VL - 29
ER -
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@article{2018_Schmidt,
author = {Elena Yur'evna Schmidt and Nadezhda Victorovna Semenova and Igor Alekseevich Ushakov and Alexander Valentinovich Vashchenko and Boris Aleksandrovich Trofimov},
title = {Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps},
journal = {Mendeleev Communications},
year = {2018},
volume = {29},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.004},
number = {1},
pages = {17--18},
doi = {10.1016/j.mencom.2019.01.004}
}
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Cite this
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Schmidt, Elena Yur'evna, et al. “Diastereoselective synthesis of 5-hydroxy-3-methylalkane-1,6-diones from ketones and acetylene in two atom-economic steps.” Mendeleev Communications, vol. 29, no. 1, Dec. 2018, pp. 17-18. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.01.004.

Abstract

(2R*,4R*)-2-Acetyl-2,6-diaryl-4-methyl-3,4-dihydropyrans (diastereoselectively synthesized from acetylene and ketones in one synthetic operation) undergo ring opening by aqueous NH4Cl (MeCN, 80°C, 8h) to afford diastereomerically pure 5-hydroxy-1,6-diketones in 48–89% yields.

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