volume 46 issue 2 pages 599-606

Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst

Zeynep Dilşad Susam 1
Merve Bozdemir 1
Gulsum Gundogdu 2
Cihangir Tanyeli 1
2
 
Turkish-German University, Faculty of Science, Department of Energy Science and Technology, 34820, Beykoz, Istanbul, Turkey
Publication typeJournal Article
Publication date2022-01-01
scimago Q2
wos Q3
SJR0.493
CiteScore5.0
Impact factor2.5
ISSN11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Abstract
Asymmetric organocatalytic domino type Michael-SN2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of α-bromonitroalkenes and 1,3-dicarbonyl compounds were allowed to react under optimized conditions, in the presence of a bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalyst. The conditions developed in this article have great advantages over the methods known in the literature in terms of reaction duration (1–6 h vs. 24–96 h) and reaction temperature (room temperature vs. −20 °C to −50 °C) giving rise to quite diastereoselective products with good enantioselectivities up to 97% ee.
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Susam Z. D. et al. Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst // New Journal of Chemistry. 2022. Vol. 46. No. 2. pp. 599-606.
GOST all authors (up to 50) Copy
Susam Z. D., Bozdemir M., Gundogdu G., Tanyeli C. Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst // New Journal of Chemistry. 2022. Vol. 46. No. 2. pp. 599-606.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/d1nj05121k
UR - https://xlink.rsc.org/?DOI=D1NJ05121K
TI - Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst
T2 - New Journal of Chemistry
AU - Susam, Zeynep Dilşad
AU - Bozdemir, Merve
AU - Gundogdu, Gulsum
AU - Tanyeli, Cihangir
PY - 2022
DA - 2022/01/01
PB - Royal Society of Chemistry (RSC)
SP - 599-606
IS - 2
VL - 46
SN - 1144-0546
SN - 1369-9261
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Susam,
author = {Zeynep Dilşad Susam and Merve Bozdemir and Gulsum Gundogdu and Cihangir Tanyeli},
title = {Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst},
journal = {New Journal of Chemistry},
year = {2022},
volume = {46},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D1NJ05121K},
number = {2},
pages = {599--606},
doi = {10.1039/d1nj05121k}
}
MLA
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MLA Copy
Susam, Zeynep Dilşad, et al. “Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst.” New Journal of Chemistry, vol. 46, no. 2, Jan. 2022, pp. 599-606. https://xlink.rsc.org/?DOI=D1NJ05121K.