Lewis base activation of thioesters remains an underexplored area of acyl transfer catalysis. Cascade transformations recently disclosed by our group showed that S-aryl thioesters can be activated with amidine-based catalysts of sufficient Lewis basicity. The new rearrangement described in this presentation demonstrates that the highly Lewis basic catalyst DHIP can also activate S-phenacyl thiocinnamates initiating a sulfa-Michael-Claisen cyclization cascade giving rise to dihydrothiophene derivatives.

Lewis base-catalyzed rearrangement of S-phenacyl thioesters

2019 Spring National Meeting

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