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

Date

2021-11-01

Author

Susam, Zeynep Dilşad
Gundogdu, Gulsum
Tanyeli, Cihangir

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Asymmetric organocatalytic domino type Michael-S(N)2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of alpha-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 degrees C to -50 degrees C) giving rise to quite diastereoselective products with good enantioselectivities up to 97% ee.

URI

https://hdl.handle.net/11511/94993

Journal

NEW JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.1039/d1nj05121k

Collections

Department of Chemistry, Article

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Citation Formats

Z. D. Susam, G. Gundogdu, and C. Tanyeli, “Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst,” NEW JOURNAL OF CHEMISTRY, pp. 0–0, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/94993.