4.4 Article

Thieme Chemistry Journal Awardees - Where Are They Now? Bifunctional Organocatalysis with N-Formyl-L-Proline: A Novel Approach to Epoxide Ring Opening and Sulfide Oxidation

Journal

SYNLETT
Volume -, Issue 5, Pages 707-711

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1219363

Keywords

bifunctional organocatalysis; Lewis base-Bronsted acid; epoxides; ring opening; amino alcohols; sulfide oxidation; sulfoxides

Funding

  1. Deutsche Forschungsgemeinschaft [SPP 1179]
  2. BMBF

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A conceptually distinct approach to the aminolysis of 1,2-epoxides, which involves Lewis base-Bronsted acid catalysis employing N-formyl-L-proline as an easily accessible bifunctional organocatalyst and water as a solvent is presented. The potential of N-formyl-L-proline as organocatalyst for the sulfide oxidation reaction using aqueous hydrogen peroxide as environmentally benign and readily available oxidant is also demonstrated. Good to high yields are achieved for both reactions.

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