posted on 2017-10-24, 15:52authored byPatrick
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.