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
Тип публикации: Journal Article
Дата публикации: 1994-03-01
scimago Q3
wos Q2
white level БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
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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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.
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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 -
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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}
}
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MLA
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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.