American Chemical Society
jo7b02299_si_002.cif (1.03 MB)

Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of S‑Allyl Thioimidate Salts

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posted on 2017-10-24, 15:52 authored by Patrick D. Parker, Bérénice C. Lemercier, Joshua G. Pierce
An efficient synthesis of S-allyl thioimidate hydrobromide salts via coupling of thioamides with allyl bromide derivatives is described. A range of mono-, di-, and trisubstituted olefins as well as alkyl- and arylthioamides with variations in electronics are tolerated. A rapid anti-diastereoselective halocyclization of these salts provides a variety of substituted alkyl- and arylthiazolines. Initial development of an efficient enantioselective synthesis of quaternary-substituted thiazolines through the organo-catalyzed halocyclization of sulfonate thioimidate salts is also described.