The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

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2021-02-01

Author

Tözendemir, Deniz
Tanyeli, Cihangir

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Cinchona alkaloid-derived organocatalysts are widely employed in various asymmetric transformations, yielding products with high enantiopurity. In this respect, a bifunctional quinine-derived sulfonamide organocatalyst was developed to catalyze the asymmetric sulfa-Michael reaction of naphthalene-1-thiol withtrans-chalcone derivatives. The target sulfa-Michael adducts were obtained with up to 96% ee under mild conditions and with a low (1 mol %) catalyst loading. Selected enantiomerically enriched sulfa-Michael addition products were subjected to oxidation to obtain the corresponding sulfones.

URI

https://hdl.handle.net/11511/88927

Journal

Beilstein Journal Of Organic Chemistry

DOI

https://doi.org/10.3762/bjoc.17.43

Collections

Department of Chemistry, Article

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Citation Formats

D. Tözendemir and C. Tanyeli, “The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst,” Beilstein Journal Of Organic Chemistry, pp. 494–503, 2021, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/88927.