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

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Tozendemir D., TANYELİ C.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.17, pp.494-503, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 17
  • Publication Date: 2021
  • Doi Number: 10.3762/bjoc.17.43
  • Journal Name: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Page Numbers: pp.494-503
  • Keywords: asymmetric synthesis, bifunctional catalysis, cinchona alkaloids, organocatalysis, sulfa-Michael reaction, CONJUGATE ADDITION, ASYMMETRIC-SYNTHESIS, BIOLOGICAL-ACTIVITY, THIOLS, SULFONES, DERIVATIVES, INHIBITORS, CHALCONES, ACCESS, DESYMMETRIZATION
  • Middle East Technical University Affiliated: Yes

Abstract

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 with trans-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.