Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides
Andreas Eitzinger
1, 2, 3, 4, 5
,
Michael Winter
1, 2, 3, 4, 5
,
Johannes Schörgenhumer
1, 2, 3, 4, 5
,
Mario Waser
1, 2, 3, 4, 5
3
Institute of Organic Chemistry
4
4040 Linz
|
5
Austria
|
Publication type: Journal Article
Publication date: 2020-01-01
scimago Q1
wos Q2
SJR: 1.037
CiteScore: 7.4
Impact factor: 4.2
ISSN: 13597345, 1364548X
PubMed ID:
31830176
Materials Chemistry
Metals and Alloys
Surfaces, Coatings and Films
General Chemistry
Ceramics and Composites
Electronic, Optical and Magnetic Materials
Catalysis
Abstract
The highly enantioselective (>99.5% ee) synthesis of a new class of densely functionalized β2,2-amino acid derivatives by reacting isoxazolidin-5-ones with para-quinone methides in the presence of chiral ammonium salt phase-transfer catalysts was developed. The reaction proceeds with exceptionally low catalyst loadings down to 20 ppm on gram scale and the utilization of the primary addition products towards further manipulations was demonstrated for selected examples.
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Total citations:
44
Citations from 2025:
3
(6.82%)
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GOST
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Eitzinger A. et al. Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides // Chemical Communications. 2020. Vol. 56. No. 4. pp. 579-582.
GOST all authors (up to 50)
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Eitzinger A., Winter M., Schörgenhumer J., Waser M. Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides // Chemical Communications. 2020. Vol. 56. No. 4. pp. 579-582.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/c9cc09239k
UR - https://xlink.rsc.org/?DOI=C9CC09239K
TI - Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides
T2 - Chemical Communications
AU - Eitzinger, Andreas
AU - Winter, Michael
AU - Schörgenhumer, Johannes
AU - Waser, Mario
PY - 2020
DA - 2020/01/01
PB - Royal Society of Chemistry (RSC)
SP - 579-582
IS - 4
VL - 56
PMID - 31830176
SN - 1359-7345
SN - 1364-548X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2020_Eitzinger,
author = {Andreas Eitzinger and Michael Winter and Johannes Schörgenhumer and Mario Waser},
title = {Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides},
journal = {Chemical Communications},
year = {2020},
volume = {56},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=C9CC09239K},
number = {4},
pages = {579--582},
doi = {10.1039/c9cc09239k}
}
Cite this
MLA
Copy
Eitzinger, Andreas, et al. “Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.” Chemical Communications, vol. 56, no. 4, Jan. 2020, pp. 579-582. https://xlink.rsc.org/?DOI=C9CC09239K.