Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity

Date

2022-10-01

Author

Susam, Zeynep Dilşad
Ozcan, Bilge Deniz
Kurtkaya, Enis
Yıldırım, Erol
Tanyeli, Cihangir

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Squaramide/cinchona alkaloid-derived bifunctional organocatalysts are in high demand in asymmetric transformations. Bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalysts were used to catalyze the asymmetric Friedel-Crafts/S(N)2 type domino reaction of (Z)-alpha-bromonitroalkenes and alpha/beta-naphthols and phenol derivatives to generate enantiomerically enriched dihydronaphthofuran (DHN) and dihydrobenzofuran (DHB) derivatives, respectively. The target adducts were obtained in up to >99% ee under mild conditions with a relatively low catalyst loading (5 mol%) compared to the methods known in the literature. In addition, density functional theory (DFT) calculations were performed to establish a possible outcome, explaining the origin of the stereoselectivity. It was discovered that pi-stacked interactions for the trans-conformation in the Friedel-Crafts step are 0.79 kcal mol(-1) more stable than the cis-conformation.

URI

https://hdl.handle.net/11511/99852

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY

DOI

https://doi.org/10.1039/d2ob01571d

Collections

Department of Chemistry, Article

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Citation Formats

Z. D. Susam, B. D. Ozcan, E. Kurtkaya, E. Yıldırım, and C. Tanyeli, “Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity,” ORGANIC & BIOMOLECULAR CHEMISTRY, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: https://hdl.handle.net/11511/99852.