Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines
1
The Dyson Perrins Laboratory, South Parks Road, Oxford,, OX1 3QY, UK
|
2
Glaxo Group Research, Ware, Herts, SG12 0DJ, UK
|
Тип публикации: Journal Article
Дата публикации: 1990-01-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
Acid promoted cyclisation of homochiral (R)-N-(3,4-dimethoxyphenethyl)-halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1,2,4,5-tetrahydrobenz[d]azepine (e.e. 6%). Coordination of the cyclisation precursor to the tricarbonylchromium(0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1 -phenyl-N-methyl-1,2,4,5-tetrahydrobenz[d]azepine. (−)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated cyclisation to furnish trans-(−)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer. In contrast, the epimeric cyclisation precursor (−)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises to give a mixture (ratio 91:9) of trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine. However, cyclisation of the tricarbonylchromium(0) complex of(−)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is completely stercoselective to yield trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine after decomplexation.
Найдено
Ничего не найдено, попробуйте изменить настройки фильтра.
Найдено
Ничего не найдено, попробуйте изменить настройки фильтра.
Топ-30
Журналы
|
1
2
3
4
5
|
|
|
Tetrahedron
5 публикаций, 19.23%
|
|
|
Tetrahedron Letters
2 публикации, 7.69%
|
|
|
Tetrahedron Asymmetry
2 публикации, 7.69%
|
|
|
Organic Process Research and Development
1 публикация, 3.85%
|
|
|
Journal of Chemical Crystallography
1 публикация, 3.85%
|
|
|
Journal of Organometallic Chemistry
1 публикация, 3.85%
|
|
|
Mendeleev Communications
1 публикация, 3.85%
|
|
|
ChemInform
1 публикация, 3.85%
|
|
|
Archiv der Pharmazie
1 публикация, 3.85%
|
|
|
European Journal of Organic Chemistry
1 публикация, 3.85%
|
|
|
Chemistry - An Asian Journal
1 публикация, 3.85%
|
|
|
Organic Letters
1 публикация, 3.85%
|
|
|
Journal of Structural Chemistry
1 публикация, 3.85%
|
|
|
Progress in Heterocyclic Chemistry
1 публикация, 3.85%
|
|
|
Russian Chemical Reviews
1 публикация, 3.85%
|
|
|
1
2
3
4
5
|
Издатели
|
2
4
6
8
10
12
14
|
|
|
Elsevier
13 публикаций, 50%
|
|
|
Wiley
4 публикации, 15.38%
|
|
|
American Chemical Society (ACS)
2 публикации, 7.69%
|
|
|
Springer Nature
1 публикация, 3.85%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 публикация, 3.85%
|
|
|
Pleiades Publishing
1 публикация, 3.85%
|
|
|
Cold Spring Harbor Laboratory
1 публикация, 3.85%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 публикация, 3.85%
|
|
|
2
4
6
8
10
12
14
|
- Мы не учитываем публикации, у которых нет DOI.
- Статистика публикаций обновляется еженедельно.
Вы ученый?
Создайте профиль, чтобы получать персональные рекомендации коллег, конференций и новых статей.
Метрики
26
Всего цитирований:
26
Цитирований c 2024:
1
(3.85%)
Цитировать
ГОСТ |
RIS |
BibTex |
MLA
Цитировать
ГОСТ
Скопировать
Coote S. J. et al. Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines // Tetrahedron Asymmetry. 1990. Vol. 1. No. 1. pp. 33-56.
ГОСТ со всеми авторами (до 50)
Скопировать
Coote S. J., Davies S. J., Middlemiss D., Naylor A. Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines // Tetrahedron Asymmetry. 1990. Vol. 1. No. 1. pp. 33-56.
Цитировать
RIS
Скопировать
TY - JOUR
DO - 10.1016/S0957-4166(00)82268-5
UR - https://doi.org/10.1016/S0957-4166(00)82268-5
TI - Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines
T2 - Tetrahedron Asymmetry
AU - Coote, Steven J.
AU - Davies, Stephen J.
AU - Middlemiss, David
AU - Naylor, Alan
PY - 1990
DA - 1990/01/01
PB - Elsevier
SP - 33-56
IS - 1
VL - 1
SN - 0957-4166
SN - 1362-511X
ER -
Цитировать
BibTex (до 50 авторов)
Скопировать
@article{1990_Coote,
author = {Steven J. Coote and Stephen J. Davies and David Middlemiss and Alan Naylor},
title = {Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines},
journal = {Tetrahedron Asymmetry},
year = {1990},
volume = {1},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0957-4166(00)82268-5},
number = {1},
pages = {33--56},
doi = {10.1016/S0957-4166(00)82268-5}
}
Цитировать
MLA
Скопировать
Coote, Steven J., et al. “Tricarbonylchromium(0) promoted stereoselective cyclisations of the N-3,4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydrobenzazepines.” Tetrahedron Asymmetry, vol. 1, no. 1, Jan. 1990, pp. 33-56. https://doi.org/10.1016/S0957-4166(00)82268-5.