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Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones

Olga Vladimirovna Gulyakevich 1
Olga Vladimirovna Gulyakevich
, 
Irene Leonovna Rubinova 1
Irene Leonovna Rubinova
, 
Dmitry Bronislavovich Rubinov 1
Dmitry Bronislavovich Rubinov
, 
Alla A Govorova 1
Alla A Govorova
, 
Alexander S Lyakhov 1
Alexander S Lyakhov
, 
Alexander Leonidovich Mikhal'chuk 1
Alexander Leonidovich Mikhal'chuk
10.1070/MC1999v009n03ABEH001065
Published 1999-05-27
Communication , Volume 9, Issue 3, 119-121
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Gulyakevich O. V. et al. Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones // Mendeleev Communications. 1999. Vol. 9. No. 3. pp. 119-121.
GOST all authors (up to 50) Copy
Gulyakevich O. V., Rubinova I. L., Rubinov D. B., Govorova A. A., Lyakhov A. S., Mikhal'chuk A. L. Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones // Mendeleev Communications. 1999. Vol. 9. No. 3. pp. 119-121.
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TY - JOUR
DO - 10.1070/MC1999v009n03ABEH001065
UR - https://mendcomm.colab.ws/publications/10.1070/MC1999v009n03ABEH001065
TI - Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones
T2 - Mendeleev Communications
AU - Gulyakevich, Olga Vladimirovna
AU - Rubinova, Irene Leonovna
AU - Rubinov, Dmitry Bronislavovich
AU - Govorova, Alla A
AU - Lyakhov, Alexander S
AU - Mikhal'chuk, Alexander Leonidovich
PY - 1999
DA - 1999/05/27
PB - Mendeleev Communications
SP - 119-121
IS - 3
VL - 9
ER -
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@article{1999_Gulyakevich,
author = {Olga Vladimirovna Gulyakevich and Irene Leonovna Rubinova and Dmitry Bronislavovich Rubinov and Alla A Govorova and Alexander S Lyakhov and Alexander Leonidovich Mikhal'chuk},
title = {Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones},
journal = {Mendeleev Communications},
year = {1999},
volume = {9},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1999v009n03ABEH001065},
number = {3},
pages = {119--121},
doi = {10.1070/MC1999v009n03ABEH001065}
}
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Gulyakevich, Olga Vladimirovna, et al. “Stereoselectivity of the annelation of 3,4-dihydroisoquinolines by 5-monosubstituted 2-acylcyclohexane-1,3-diones.” Mendeleev Communications, vol. 9, no. 3, May. 1999, pp. 119-121. https://mendcomm.colab.ws/publications/10.1070/MC1999v009n03ABEH001065.

Abstract

The annelation of 1-methyl-3,4-dihydroisoquinoline by prochiral 5-substituted 2-acylcyclohexane-1,3-diones proceeds diastereoselectively yielding a 9R,16R:9S,16S pair of enantiomers rather than a possible mixture of four 8-aza-D-homogona-12,17a-dione stereoisomers; this stereoselectivity results from the impossibility of a threo-attack on the prochiral β,β’-triketone by azomethyne owing to the spatial structure of 2-acylcyclohexane-1,3-dione, on the one hand, and by the steric effect of the C(1) methyl group of 3,4-dihydroisoquinoline, on the other.

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