Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.
Publication type: Journal Article
Publication date: 1993-04-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
N-tosyl-oxiraneethylamines undergo cyclization upon treatment with aqueous sodium hydroxide to afford either N-tosyl-azetidinemethanols or N-tosyl-pyrrolidin-3-ols in high yields. The change in regioselectivity of this cyclization process is quite dependent on the location of a pentamethylene substitution in the chain connecting the nitrogen with the oxirane ring.
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17
Total citations:
17
Citations from 2024:
1
(5.88%)
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GOST
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Moulines J. et al. Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization. // Tetrahedron Letters. 1993. Vol. 34. No. 14. pp. 2315-2318.
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Moulines J., Bats J. P., Hautefaye P., Nührich A., Lamidey A. M. Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization. // Tetrahedron Letters. 1993. Vol. 34. No. 14. pp. 2315-2318.
Cite this
RIS
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TY - JOUR
DO - 10.1016/s0040-4039(00)77602-7
UR - https://doi.org/10.1016/s0040-4039(00)77602-7
TI - Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.
T2 - Tetrahedron Letters
AU - Moulines, Jean
AU - Bats, Jean Paul
AU - Hautefaye, Patrick
AU - Nührich, Alain
AU - Lamidey, Anne Marie
PY - 1993
DA - 1993/04/01
PB - Elsevier
SP - 2315-2318
IS - 14
VL - 34
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
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@article{1993_Moulines,
author = {Jean Moulines and Jean Paul Bats and Patrick Hautefaye and Alain Nührich and Anne Marie Lamidey},
title = {Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.},
journal = {Tetrahedron Letters},
year = {1993},
volume = {34},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/s0040-4039(00)77602-7},
number = {14},
pages = {2315--2318},
doi = {10.1016/s0040-4039(00)77602-7}
}
Cite this
MLA
Copy
Moulines, Jean, et al. “Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization..” Tetrahedron Letters, vol. 34, no. 14, Apr. 1993, pp. 2315-2318. https://doi.org/10.1016/s0040-4039(00)77602-7.