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Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides

Rauf Talgatovich Akhmirov 1, 2
Rauf Talgatovich Akhmirov
, 
Sema Leibovich Ioffe 1
Sema Leibovich Ioffe
, 
Alexey Yu Sukhorukov 1
Alexey Yu Sukhorukov
10.1016/j.mencom.2021.09.031
Published 2021-09-08
Communication , Volume 31, Issue 5, 686-689
2
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Akhmirov R. T., Ioffe S. L., Sukhorukov A. Yu. Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 686-689.
GOST all authors (up to 50) Copy
Akhmirov R. T., Ioffe S. L., Sukhorukov A. Yu. Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 686-689.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.031
TI - Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides
T2 - Mendeleev Communications
AU - Akhmirov, Rauf Talgatovich
AU - Ioffe, Sema Leibovich
AU - Sukhorukov, Alexey Yu
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 686-689
IS - 5
VL - 31
ER -
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@article{2021_Akhmirov,
author = {Rauf Talgatovich Akhmirov and Sema Leibovich Ioffe and Alexey Yu Sukhorukov},
title = {Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.031},
number = {5},
pages = {686--689},
doi = {10.1016/j.mencom.2021.09.031}
}
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Akhmirov, Rauf Talgatovich, et al. “Stereoselective approach to conjugated enone oximes from aliphatic nitro compounds and sulfur ylides.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 686-689. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.031.

Keywords

Michael addition
nitro compounds
nitrosoalkenes
unsaturated oximes
ylides

Abstract

A novel approach to conjugated enone oximes from aliphatic nitro compounds deals with double silylation of N,N-bis(silyloxy) enamines followed by a stereoselective reaction with an ester-stabilized sulfur ylide. The proposed mechanism involves the generation of labile nitrosoalkenes as intermediates, which react with the sulfur ylide to give target enone oximes.

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