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Organocatalyzed Rearrangement of S‑(2-Oxoalkyl)-thioenoates

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journal contribution
posted on 17.05.2019, 00:00 by David M. Leace, Matthew R. Straub, Benjamin A. Matz, Vladimir B. Birman
The highly Lewis basic amidine-based catalyst DHIP promotes the rearrangement of S-phenacyl thiocinnamate and related thioesters into dihydrothiophene derivatives. In contrast to previously explored rearrangements of thioesters, the reaction proceeds via a novel Dieckmann-like cyclization pathway. An alternative two-component synthesis of the same products has also been developed.