The Synthesis of Chiral β-Naphthyl-β-Sulfanyl Ketones via Enantioselective Sulfa-Michael Reaction in the Presence of a Bifunctional Cinchona/Sulfonamide Organocatalyst

  1. Deniz Tözendemir and
  2. Cihangir TanyeliORCID Logo

Submitting author affiliation: Middle East Technical University Department of Chemistry 06800 Ankara, Ankara, Turkey

Beilstein Arch. 2020, 2020129. https://doi.org/10.3762/bxiv.2020.129.v1

Published 12 Nov 2020

  • Preprint

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 SMA products were subjected to oxidation to obtain corresponding sulfones.

Keywords: asymmetric synthesis; organocatalysis; sulfa-Michael reaction; cinchona alkaloids; bifunctional catalysis

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Tözendemir, D.; Tanyeli, C. Beilstein Arch. 2020, 2020129. doi:10.3762/bxiv.2020.129.v1

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© 2020 Tözendemir and Tanyeli; licensee Beilstein-Institut.
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