Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution
Osamu TAMURA
1
,
Masaru Hashimoto
1
,
Yuko Kobayashi
1
,
Tadashi Katoh
1
,
K. Nakatani
1
,
Masahiro Kamada
2
,
Isao Hayakawa
3
,
TOSHIFUMI AKIBA
2
,
Shiro Terashima
1
1
Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229, Japan
|
2
Production Technology Research Laboratories, Daiichi Pharmaceutical Co., Ltd., Kita-Kasai, Edogawa, Tokyo 134, Japan
|
3
Exploratory Research Laboratories, Daiichi Pharmaceutical Co., Ltd., Kita-Kasai, Edogawa, Tokyo 134, Japan
|
Publication type: Journal Article
Publication date: 1994-03-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The title synthesis was achieved by employing highly cis-selective cyclopropanation of N-benzyl-N-vinylcarbamates with zinc-monofluorocarbenoid, deprotection of the formed N-benzyl-N-(cis-2-fluorocyclopropyl)carbamates, and optical resolution of the resulting dl-cis-2-fluorocyclopropylamine by the use of l-menthyl chloroformate as a resolving agent. The cis-selectivity observed for the key cyclopropanation could be explained by the bent transition state model.
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37
Total citations:
37
Citations from 2024:
3
(8.11%)
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TAMURA O. et al. Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution // Tetrahedron. 1994. Vol. 50. No. 13. pp. 3889-3904.
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TAMURA O., Hashimoto M., Kobayashi Y., Katoh T., Nakatani K., Kamada M., Hayakawa I., AKIBA T., Terashima S. Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution // Tetrahedron. 1994. Vol. 50. No. 13. pp. 3889-3904.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0040-4020(01)89665-4
UR - https://doi.org/10.1016/S0040-4020(01)89665-4
TI - Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution
T2 - Tetrahedron
AU - TAMURA, Osamu
AU - Hashimoto, Masaru
AU - Kobayashi, Yuko
AU - Katoh, Tadashi
AU - Nakatani, K.
AU - Kamada, Masahiro
AU - Hayakawa, Isao
AU - AKIBA, TOSHIFUMI
AU - Terashima, Shiro
PY - 1994
DA - 1994/03/01
PB - Elsevier
SP - 3889-3904
IS - 13
VL - 50
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{1994_TAMURA,
author = {Osamu TAMURA and Masaru Hashimoto and Yuko Kobayashi and Tadashi Katoh and K. Nakatani and Masahiro Kamada and Isao Hayakawa and TOSHIFUMI AKIBA and Shiro Terashima},
title = {Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution},
journal = {Tetrahedron},
year = {1994},
volume = {50},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/S0040-4020(01)89665-4},
number = {13},
pages = {3889--3904},
doi = {10.1016/S0040-4020(01)89665-4}
}
Cite this
MLA
Copy
TAMURA, Osamu, et al. “Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution.” Tetrahedron, vol. 50, no. 13, Mar. 1994, pp. 3889-3904. https://doi.org/10.1016/S0040-4020(01)89665-4.