Catalytic Enantioselective Alkylation of Sulfenate Anions to Chiral Heterocyclic Sulfoxides

Using Halogenated Pentanidium Salts

Lili Zong, Xu Ban, Choon Wee Kee and Prof. Dr. Choon‐Hong Tan

Angewandte Chemie International Edition, 2014, 53, 11849 – 11853. (Highlighted by Synfacts 2014, 10, 1322; contributors: Benjamin List, Mattia Riccardo Monaco)

Abstract: We report halogenated pentanidiums as phase‐transfer catalysts for the asymmetric alkylation of sulfenate anions to various sulfoxides with high enantioselectivities (up to 99 % ee) and yields (up to 99 %). This approach gives access to enantioenriched heterocyclic sulfoxides that might not be compatible with strong oxidants or organometallic reagents. Computational studies have revealed that the multiple noncovalent interactions such as halogen bonds and nonclassical hydrogen bonds are involved.

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