Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine
Publication type: Journal Article
Publication date: 1993-10-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
A new synthetic route to (2S,5S)-dimethylpyrrolidine 1, which can also be applied to the synthesis of the (2R,5R)-enantiomer, has been developed. The C2-symmetric pyrrolidine can be obtained enantiomerically pure (e.e. ⩾ 97%) in 15% overall yield starting from a mixture of isomers of 2,5-hexanediol, via a short reaction sequence using (S)-α-methylbenzylamine as a chiral auxiliary. The crystal and molecular structure of (S)-2′-phenyl-N-ethyl-(2S,5S)-dimethylpyrrolidine picrate 5, showing an antiparallel stacking of the picrate units, is also reported.
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Zwaagstra M. E., Meetsma A., Feringa B. L. Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine // Tetrahedron Asymmetry. 1993. Vol. 4. No. 10. pp. 2163-2172.
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Zwaagstra M. E., Meetsma A., Feringa B. L. Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine // Tetrahedron Asymmetry. 1993. Vol. 4. No. 10. pp. 2163-2172.
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TY - JOUR
DO - 10.1016/S0957-4166(00)80066-X
UR - https://doi.org/10.1016/S0957-4166(00)80066-X
TI - Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine
T2 - Tetrahedron Asymmetry
AU - Zwaagstra, Mariel E.
AU - Meetsma, Auke
AU - Feringa, Ben L.
PY - 1993
DA - 1993/10/01
PB - Elsevier
SP - 2163-2172
IS - 10
VL - 4
SN - 0957-4166
SN - 1362-511X
ER -
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@article{1993_Zwaagstra,
author = {Mariel E. Zwaagstra and Auke Meetsma and Ben L. Feringa},
title = {Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine},
journal = {Tetrahedron Asymmetry},
year = {1993},
volume = {4},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/S0957-4166(00)80066-X},
number = {10},
pages = {2163--2172},
doi = {10.1016/S0957-4166(00)80066-X}
}
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MLA
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Zwaagstra, Mariel E., et al. “Asymmetric synthesis of Trans-2,5-dimethylpyrrolidine.” Tetrahedron Asymmetry, vol. 4, no. 10, Oct. 1993, pp. 2163-2172. https://doi.org/10.1016/S0957-4166(00)80066-X.