Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation
Ramon J Alabaster
1
,
Andrew Gibson
1
,
Simon A. Johnson
1
,
John John D. Edwards
1
,
Ian F. Cottrell
1
1
Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, UK
|
Publication type: Journal Article
Publication date: 1997-02-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The simple and efficient preparation of enantiomerically pure N -benzyl-3-( S )-(+)-(4-fluorophenyl)-1,4-oxazin-2-one by a crystallisation induced asymmetric transformation of its racemate is reported. A key feature of this process is the use of [(1 S )-(endo,anti)]-(−)-3-bromocamphor-8-sulfonic acid as both resolving agent for the pure ( S )-enantiomer, and in situ racemising agent of the unwanted enantiomer, affording the title compound in high yield. A simple and efficient preparation of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one from its racemate is reported. A key feature of this process is the use of [(1S)-(endo,anti)]-(−)-3-bromocamphor-8-sulfonic acid as both resolving agent for the pure (S)-enantiomer, and in situ racemising agent of the unwanted enantiomer.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Organic Process Research and Development
2 publications, 12.5%
|
|
|
Journal of Organic Chemistry
2 publications, 12.5%
|
|
|
Synthetic Communications
2 publications, 12.5%
|
|
|
Organic Letters
1 publication, 6.25%
|
|
|
Beilstein Journal of Organic Chemistry
1 publication, 6.25%
|
|
|
Tetrahedron Asymmetry
1 publication, 6.25%
|
|
|
Drug Discovery Today
1 publication, 6.25%
|
|
|
Chemistry - A European Journal
1 publication, 6.25%
|
|
|
Chemical Reviews
1 publication, 6.25%
|
|
|
Heterocycles
1 publication, 6.25%
|
|
|
Strategies and Tactics in Organic Synthesis
1 publication, 6.25%
|
|
|
Topics in Current Chemistry
1 publication, 6.25%
|
|
|
1
2
|
Publishers
|
1
2
3
4
5
6
|
|
|
American Chemical Society (ACS)
6 publications, 37.5%
|
|
|
Elsevier
3 publications, 18.75%
|
|
|
Taylor & Francis
2 publications, 12.5%
|
|
|
Beilstein-Institut
1 publication, 6.25%
|
|
|
Wiley
1 publication, 6.25%
|
|
|
The Japan Institute of Heterocyclic Chemistry
1 publication, 6.25%
|
|
|
Springer Nature
1 publication, 6.25%
|
|
|
1
2
3
4
5
6
|
- 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
16
Total citations:
16
Citations from 2024:
0
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Alabaster R. J. et al. Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation // Tetrahedron Asymmetry. 1997. Vol. 8. No. 3. pp. 447-450.
GOST all authors (up to 50)
Copy
Alabaster R. J., Gibson A., Johnson S. A., John D. Edwards J., Cottrell I. F. Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation // Tetrahedron Asymmetry. 1997. Vol. 8. No. 3. pp. 447-450.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/S0957-4166(96)00531-9
UR - https://doi.org/10.1016/S0957-4166(96)00531-9
TI - Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation
T2 - Tetrahedron Asymmetry
AU - Alabaster, Ramon J
AU - Gibson, Andrew
AU - Johnson, Simon A.
AU - John D. Edwards, John
AU - Cottrell, Ian F.
PY - 1997
DA - 1997/02/01
PB - Elsevier
SP - 447-450
IS - 3
VL - 8
SN - 0957-4166
SN - 1362-511X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1997_Alabaster,
author = {Ramon J Alabaster and Andrew Gibson and Simon A. Johnson and John John D. Edwards and Ian F. Cottrell},
title = {Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation},
journal = {Tetrahedron Asymmetry},
year = {1997},
volume = {8},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/S0957-4166(96)00531-9},
number = {3},
pages = {447--450},
doi = {10.1016/S0957-4166(96)00531-9}
}
Cite this
MLA
Copy
Alabaster, Ramon J., et al. “Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via a crystallisation induced asymmetric transformation.” Tetrahedron Asymmetry, vol. 8, no. 3, Feb. 1997, pp. 447-450. https://doi.org/10.1016/S0957-4166(96)00531-9.