A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry
Publication type: Journal Article
Publication date: 1993-01-01
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Catalysis
Organic Chemistry
Abstract
By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromoadipate and separated by crystallization and chromatographic fractionation involving stereoselective hydrolysis. The cis isomer is recovered and epimerized to the trans counterparts. Starting from each of the two trans isomers, optically active 2,5-disubstituted [2,5-bis(methoxymethyl) and 2,5-bis(methoxymethoxymetbyl)] pyrrolidines of C 2 -symmetry are synthesized by a short route
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Yamamoto Y. et al. A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry // Synthesis. 1993. Vol. 1993. No. 03. pp. 298-302.
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Yamamoto Y., Hoshino J., Fujimoto Y., Ohmoto J., Sawada S. A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry // Synthesis. 1993. Vol. 1993. No. 03. pp. 298-302.
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RIS
Copy
TY - JOUR
DO - 10.1055/s-1993-25852
UR - https://doi.org/10.1055/s-1993-25852
TI - A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry
T2 - Synthesis
AU - Yamamoto, Yukio
AU - Hoshino, Junichi
AU - Fujimoto, Yukiko
AU - Ohmoto, Junko
AU - Sawada, Seiji
PY - 1993
DA - 1993/01/01
PB - Georg Thieme Verlag KG
SP - 298-302
IS - 03
VL - 1993
SN - 0039-7881
SN - 1437-210X
ER -
Cite this
BibTex (up to 50 authors)
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@article{1993_Yamamoto,
author = {Yukio Yamamoto and Junichi Hoshino and Yukiko Fujimoto and Junko Ohmoto and Seiji Sawada},
title = {A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry},
journal = {Synthesis},
year = {1993},
volume = {1993},
publisher = {Georg Thieme Verlag KG},
month = {jan},
url = {https://doi.org/10.1055/s-1993-25852},
number = {03},
pages = {298--302},
doi = {10.1055/s-1993-25852}
}
Cite this
MLA
Copy
Yamamoto, Yukio, et al. “A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry.” Synthesis, vol. 1993, no. 03, Jan. 1993, pp. 298-302. https://doi.org/10.1055/s-1993-25852.