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Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes

Valentin Dmitrievich Gvozdev 1
Valentin Dmitrievich Gvozdev
, 
Konstantin Nikolaevich Shavrin 1
Konstantin Nikolaevich Shavrin
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
, 
Oleg Matveevich Nefedov 1
Oleg Matveevich Nefedov
10.1016/j.mencom.2021.09.020
Published 2021-09-08
Communication , Volume 31, Issue 5, 654-656
5
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Gvozdev V. D. et al. Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 654-656.
GOST all authors (up to 50) Copy
Gvozdev V. D., Shavrin K. N., Egorov M. P., Nefedov O. M. Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 654-656.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.020
TI - Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes
T2 - Mendeleev Communications
AU - Gvozdev, Valentin Dmitrievich
AU - Shavrin, Konstantin Nikolaevich
AU - Egorov, Mikhail Petrovich
AU - Nefedov, Oleg Matveevich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 654-656
IS - 5
VL - 31
ER -
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@article{2021_Gvozdev,
author = {Valentin Dmitrievich Gvozdev and Konstantin Nikolaevich Shavrin and Mikhail Petrovich Egorov and Oleg Matveevich Nefedov},
title = {Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.020},
number = {5},
pages = {654--656},
doi = {10.1016/j.mencom.2021.09.020}
}
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Gvozdev, Valentin Dmitrievich, et al. “Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 654-656. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.020.

Keywords

1-amino-2-alkynylcyclopropanes
alkylation
alkynyl(chloro)cyclopropanes
cyclopropenes
cyclopropylamines
directing groups
lithiation
protecting groups
stereoselectivity

Abstract

New N-Boc-alkyl(2-alkynylcyclopropyl)amines were synthesized from 1-alkynyl-1-chlorocyclopropanes and N-Boc- alkylamines under the action of ButOK in DMSO, the intermediates having been the corresponding conjugated alkynylcyclopropenes. The Boc-derivatives can be converted into free secondary 2-alkynylcyclopropylamines, as well as β-lithiated with subsequent alkylation.

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