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
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2
Glaxo Group Research, Ware, Herts, SG12 0DJ, UK
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Publication type: Journal Article
Publication date: 1990-01-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
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.
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Total citations:
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Citations from 2024:
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(3.85%)
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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.
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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.
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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 -
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BibTex (up to 50 authors)
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@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}
}
Cite this
MLA
Copy
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.