Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines
Publication type: Journal Article
Publication date: 2010-03-01
scimago Q2
wos Q2
SJR: 0.751
CiteScore: 5.9
Impact factor: 3.3
ISSN: 18614728, 1861471X
PubMed ID:
20146283
General Chemistry
Organic Chemistry
Biochemistry
Abstract
The acid-promoted cyclizations of a range of N-benzylethanolamines (derived from pseudoephedrine or ephedrine) give the corresponding trans-N(2),3-dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines with high levels of diastereoselectivity and in good yields of isolated product. The cyclizations of the corresponding chromium tricarbonyl complexes are rendered completely stereoselective. Acid-promoted cyclization of N-(3',4'-dimethoxybenzyl)ephedrine and its chromium tricarbonyl complex occur with complementary diastereoselectivities to give trans- and cis-N(2),3-dimethyl-4-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline, respectively, in >99:1 d.r. The latter is consistent with a double inversion mechanism, which involves neighboring group participation by the chromium tricarbonyl moiety followed by rearomatization to give the corresponding cis-tetrahydroisoquinoline with overall retention of configuration.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
|
|
|
Tetrahedron
3 publications, 15.79%
|
|
|
Tetrahedron Asymmetry
2 publications, 10.53%
|
|
|
Organic and Biomolecular Chemistry
2 publications, 10.53%
|
|
|
Nature Catalysis
1 publication, 5.26%
|
|
|
Tetrahedron Letters
1 publication, 5.26%
|
|
|
Angewandte Chemie - International Edition
1 publication, 5.26%
|
|
|
Angewandte Chemie
1 publication, 5.26%
|
|
|
Drug Testing and Analysis
1 publication, 5.26%
|
|
|
Chirality
1 publication, 5.26%
|
|
|
Advanced Synthesis and Catalysis
1 publication, 5.26%
|
|
|
Chemistry - An Asian Journal
1 publication, 5.26%
|
|
|
Heterocycles
1 publication, 5.26%
|
|
|
Synlett
1 publication, 5.26%
|
|
|
Russian Chemical Reviews
1 publication, 5.26%
|
|
|
1
2
3
|
Publishers
|
1
2
3
4
5
6
7
|
|
|
Wiley
7 publications, 36.84%
|
|
|
Elsevier
6 publications, 31.58%
|
|
|
Royal Society of Chemistry (RSC)
2 publications, 10.53%
|
|
|
Springer Nature
1 publication, 5.26%
|
|
|
The Japan Institute of Heterocyclic Chemistry
1 publication, 5.26%
|
|
|
Georg Thieme Verlag KG
1 publication, 5.26%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 5.26%
|
|
|
1
2
3
4
5
6
7
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
19
Total citations:
19
Citations from 2024:
1
(5.26%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Coote S. J. et al. Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines // Chemistry - An Asian Journal. 2010. Vol. 5. No. 3. pp. 589-604.
GOST all authors (up to 50)
Copy
Coote S. J., Davies S. J., Fletcher A. M., Roberts P., Thomson J. E. Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines // Chemistry - An Asian Journal. 2010. Vol. 5. No. 3. pp. 589-604.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/asia.200900470
UR - https://doi.org/10.1002/asia.200900470
TI - Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines
T2 - Chemistry - An Asian Journal
AU - Coote, Steven J.
AU - Davies, Stephen J.
AU - Fletcher, Ai M.
AU - Roberts, Paul.M.
AU - Thomson, James E.
PY - 2010
DA - 2010/03/01
PB - Wiley
SP - 589-604
IS - 3
VL - 5
PMID - 20146283
SN - 1861-4728
SN - 1861-471X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2010_Coote,
author = {Steven J. Coote and Stephen J. Davies and Ai M. Fletcher and Paul.M. Roberts and James E. Thomson},
title = {Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines},
journal = {Chemistry - An Asian Journal},
year = {2010},
volume = {5},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/asia.200900470},
number = {3},
pages = {589--604},
doi = {10.1002/asia.200900470}
}
Cite this
MLA
Copy
Coote, Steven J., et al. “Enantiospecific Stereodivergent Synthesis oftrans- andcis-N(2),3-Dimethyl-4-phenyl-1,2,3,4-tetrahydroisoquinolines.” Chemistry - An Asian Journal, vol. 5, no. 3, Mar. 2010, pp. 589-604. https://doi.org/10.1002/asia.200900470.