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A stereochemical approach to the Kabachnik–Fields reaction mechanism

Mudaris Nurgaleevich Dimukhametov 1
Mudaris Nurgaleevich Dimukhametov
, 
Evgenia Vladimirovna Bayandina 1
Evgenia Vladimirovna Bayandina
, 
Elena Yur'evna Davydova 1
Elena Yur'evna Davydova
, 
Aidar Timergalievich Gubaidullin 1
Aidar Timergalievich Gubaidullin
, 
Vladimir Alekseevich Alfonsov 1
Vladimir Alekseevich Alfonsov
10.1070/MC2003v013n03ABEH001763
Published 2003-07-11
Communication , Volume 13, Issue 3, 150-151
11
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Dimukhametov M. N. et al. A stereochemical approach to the Kabachnik–Fields reaction mechanism // Mendeleev Communications. 2003. Vol. 13. No. 3. pp. 150-151.
GOST all authors (up to 50) Copy
Dimukhametov M. N., Bayandina E. V., Davydova E. Y., Gubaidullin A. T., Alfonsov V. A. A stereochemical approach to the Kabachnik–Fields reaction mechanism // Mendeleev Communications. 2003. Vol. 13. No. 3. pp. 150-151.
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TY - JOUR
DO - 10.1070/MC2003v013n03ABEH001763
UR - https://mendcomm.colab.ws/publications/10.1070/MC2003v013n03ABEH001763
TI - A stereochemical approach to the Kabachnik–Fields reaction mechanism
T2 - Mendeleev Communications
AU - Dimukhametov, Mudaris Nurgaleevich
AU - Bayandina, Evgenia Vladimirovna
AU - Davydova, Elena Yur'evna
AU - Gubaidullin, Aidar Timergalievich
AU - Alfonsov, Vladimir Alekseevich
PY - 2003
DA - 2003/07/11
PB - Mendeleev Communications
SP - 150-151
IS - 3
VL - 13
ER -
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@article{2003_Dimukhametov,
author = {Mudaris Nurgaleevich Dimukhametov and Evgenia Vladimirovna Bayandina and Elena Yur'evna Davydova and Aidar Timergalievich Gubaidullin and Vladimir Alekseevich Alfonsov},
title = {A stereochemical approach to the Kabachnik–Fields reaction mechanism},
journal = {Mendeleev Communications},
year = {2003},
volume = {13},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2003v013n03ABEH001763},
number = {3},
pages = {150--151},
doi = {10.1070/MC2003v013n03ABEH001763}
}
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Dimukhametov, Mudaris Nurgaleevich, et al. “A stereochemical approach to the Kabachnik–Fields reaction mechanism.” Mendeleev Communications, vol. 13, no. 3, Jul. 2003, pp. 150-151. https://mendcomm.colab.ws/publications/10.1070/MC2003v013n03ABEH001763.

Abstract

A comparison of the diastereomeric composition of Kabachnik–Fields reaction products with those of two reactions simulating its stereo-controlling steps showed that only the ‘imine’ mechanism works in the (MeO)2P(O)H–PhCHO-[(S),(R,S)-H2NCH(Ph)Me] system, like in the phosphite–imine system; in a similar system containing (R,S)-sec-butylamine, additional ‘nucleophilic amination’ of the initially formed α-hydroxybenzyl phosphonate occurs.

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