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One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step

Petr Aleksandrovich Zhmurov 1
Petr Aleksandrovich Zhmurov
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
, 
Olga Yurievna Bakulina 1
Olga Yurievna Bakulina
, 
Mikhail Yur'evich Krasavin 1
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2020.05.016
Published 2020-04-30
Communication , Volume 30, Issue 3, 311-312
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Zhmurov P. A. et al. One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step // Mendeleev Communications. 2020. Vol. 30. No. 3. pp. 311-312.
GOST all authors (up to 50) Copy
Zhmurov P. A., Dar’in D. V., Bakulina O. Y., Krasavin M. Y. One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step // Mendeleev Communications. 2020. Vol. 30. No. 3. pp. 311-312.
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TY - JOUR
DO - 10.1016/j.mencom.2020.05.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.016
TI - One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step
T2 - Mendeleev Communications
AU - Zhmurov, Petr Aleksandrovich
AU - Dar’in, Dmitry Viktorovich
AU - Bakulina, Olga Yurievna
AU - Krasavin, Mikhail Yur'evich
PY - 2020
DA - 2020/04/30
PB - Mendeleev Communications
SP - 311-312
IS - 3
VL - 30
ER -
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@article{2020_Zhmurov,
author = {Petr Aleksandrovich Zhmurov and Dmitry Viktorovich Dar’in and Olga Yurievna Bakulina and Mikhail Yur'evich Krasavin},
title = {One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.016},
number = {3},
pages = {311--312},
doi = {10.1016/j.mencom.2020.05.016}
}
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Zhmurov, Petr Aleksandrovich, et al. “One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step.” Mendeleev Communications, vol. 30, no. 3, Apr. 2020, pp. 311-312. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.016.

Keywords

diazo transfer
insertion reactions
methoxycarbonylation
SAFE cocktail
β-oxopropionates

Abstract

Methyl 2-diazo-3-oxopropionates were obtained by in situ methoxycarbonylation of methyl ketones followed by diazo transfer onto active methylene group of the intermediate β-oxo esters. At the second stage, ‘sulfonyl-azide-free’ (SAFE) diazo transfer protocol in aqueous medium was employed.

References

1.
Modern Organic Synthesis with α-Diazocarbonyl Compounds
Ford A., Miel H., Ring A., Slattery C.N., Maguire A.R., McKervey M.A.
Chemical Reviews, 2015
2.
10.1016/j.mencom.2020.05.016_bib0010
Doyle
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, 1998
3.
10.1016/j.mencom.2020.05.016_bib0015
Regitz
Chem., 1964
4.
10.1016/j.mencom.2020.05.016_bib0020
Regitz
Diazo Compounds: Properties and Synthesis, 1986
5.
Diazotransfer Reagents1
Bollinger F.W., Tuma L.D.
Synlett, 1996
6.
PREPARATION OFp-TOLUENESULFONYL AZIDE. A CAUTIONARY NOTE
Curphey T.J.
Organic Preparations and Procedures International, 1981
13.
Guanidinium iodide-catalyzed oxidative α-nitroalkylation of β-ketoamides
Yasui K., Kato T., Kojima K., Nagasawa K.
Chemical Communications, 2015