Reactions
The carbonyl center in thioesters is reactive toward nucleophiles, the reactivity being reminiscent of but milder than acid chlorides. Thus, thioesters and amines combine to give amides:
- Thioesters provide useful chemoselectivity in the synthesis of biomolecules.
A reaction unique to thioesters is the Fukuyama coupling, in which the thioester is coupled with an organozinc halide by a palladium catalyst to give a ketone.
The C-H groups adjacent to the carbonyl in thioesters are mildly acidic and undergo aldol condensations. This kind of reaction occurs in the biosynthesis of fatty acids.
Read more about this topic: Thioester
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