Abstract
The first N-heterocyclic carbene (NHC)-organocatalytic tandem [1,2]-phospha-Brook/[1,4]-phosphate rearrangement is reported. Acyl phosphonates, unlike acyl silanes that are well-exploited, make entry as the acyl anion precursors under NHC catalysis. The reactions proceed with absolute chemoselectivity via cross-acyloin condensation between acyl phosphonates and aldehydes giving the products α-ketophosphates in good to excellent yields. The challenging (enolizable) aliphatic-aliphatic substrates coupling also furnished the desired product in a good yield.
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