Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid
Тип публикации: Journal Article
Дата публикации: 1996-01-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Краткое описание
By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13 , in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from 1 H NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave ( S )-3-pyrrolidineacetic acid, 2 . Following the same synthetic scheme, but starting from either 11 or 13 , ( R )-3-pyrrolidineacetic acid 3 was obtained. The major isomer can be converted into ( S )-3-pyrrolidincacetic acid
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Galeazzi R. L. et al. Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid // Tetrahedron Asymmetry. 1996. Vol. 7. No. 1. pp. 79-88.
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Galeazzi R. L., Geremia S., Mobbili G., Orena M. Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid // Tetrahedron Asymmetry. 1996. Vol. 7. No. 1. pp. 79-88.
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TY - JOUR
DO - 10.1016/0957-4166(95)00423-8
UR - https://doi.org/10.1016/0957-4166(95)00423-8
TI - Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid
T2 - Tetrahedron Asymmetry
AU - Galeazzi, R. L.
AU - Geremia, Silvano
AU - Mobbili, Giovanna
AU - Orena, Mario
PY - 1996
DA - 1996/01/01
PB - Elsevier
SP - 79-88
IS - 1
VL - 7
SN - 0957-4166
SN - 1362-511X
ER -
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@article{1996_Galeazzi,
author = {R. L. Galeazzi and Silvano Geremia and Giovanna Mobbili and Mario Orena},
title = {Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid},
journal = {Tetrahedron Asymmetry},
year = {1996},
volume = {7},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/0957-4166(95)00423-8},
number = {1},
pages = {79--88},
doi = {10.1016/0957-4166(95)00423-8}
}
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MLA
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Galeazzi, R. L., et al. “Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid.” Tetrahedron Asymmetry, vol. 7, no. 1, Jan. 1996, pp. 79-88. https://doi.org/10.1016/0957-4166(95)00423-8.
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