Abstract
AbstractThe tandem nucleophilic addition‐cyclization reaction of o‐alkynylbenzaldehydes or o‐alkynylacetophenones 2 with dialkyl phosphites or dialkyl phosphonothioates 1 took place very smoothly in the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) in THF at room temperature. In all cases, the reaction proceeded in a regioselective manner leading to the 5‐exo‐dig products 3 in excellent yields. The phenomenon of a 1,5‐sigmatropic hydrogen shift or a 1,5‐sigmatropic methyl shift was observed in this reaction depending on the different substituent groups such as R3 in the o‐alkynylbenzaldehyde or o‐alkynylacetophenone 2 substrates.
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