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The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines

Edward Prokof'evich Serebryakov 1
Edward Prokof'evich Serebryakov
, 
Albert Gabidullinovich Nigmatov 1
Albert Gabidullinovich Nigmatov
, 
Mikhail Aleksandrovich Shcherbakov 1
Mikhail Aleksandrovich Shcherbakov
10.1070/MC2001v011n05ABEH001502
Published 2001-10-23
Communication , Volume 11, Issue 5, 174-175
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Serebryakov E. P., Nigmatov A. G., Shcherbakov M. A. The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines // Mendeleev Communications. 2001. Vol. 11. No. 5. pp. 174-175.
GOST all authors (up to 50) Copy
Serebryakov E. P., Nigmatov A. G., Shcherbakov M. A. The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines // Mendeleev Communications. 2001. Vol. 11. No. 5. pp. 174-175.
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TY - JOUR
DO - 10.1070/MC2001v011n05ABEH001502
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001502
TI - The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines
T2 - Mendeleev Communications
AU - Serebryakov, Edward Prokof'evich
AU - Nigmatov, Albert Gabidullinovich
AU - Shcherbakov, Mikhail Aleksandrovich
PY - 2001
DA - 2001/10/23
PB - Mendeleev Communications
SP - 174-175
IS - 5
VL - 11
ER -
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@article{2001_Serebryakov,
author = {Edward Prokof'evich Serebryakov and Albert Gabidullinovich Nigmatov and Mikhail Aleksandrovich Shcherbakov},
title = {The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001502},
number = {5},
pages = {174--175},
doi = {10.1070/MC2001v011n05ABEH001502}
}
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Serebryakov, Edward Prokof'evich, et al. “The effect of pressure on the diastereoselectivity of the reaction of prenal with monoalkyl ylidenemalonates catalysed by homochiral secondary amines.” Mendeleev Communications, vol. 11, no. 5, Oct. 2001, pp. 174-175. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n05ABEH001502.

Abstract

The dienamine-mediated formation of 6-substituted cyclohexa-1,3-dienes from the title reactants catalysed by either (S)- or (R)- prolinol at 8 kbar proceeds with different net enantioselectivities depending on the structure of RCH=C(CO2H)CO2Alk to give a product with the same configuration as that obtained at atmospheric pressure (if R = Me2C=CH) or with a configuration opposite to the latter (if R = Ph); by contrast, with both dienophiles the sense of enantioselectivity does not change with pressure when (S)-α,α-diphenyl-2-pyrrolidinemethanol is used as the catalyst.

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