By choosing the organic acid catalysts, the reaction of lactones with ketene silyl acetals results in selective formation of simple Mukaiyama aldol adducts or olefination products, which are formed by the subsequent elimination of a silanol from the adducts. That is, in the presence of acidic zwitterions, the reaction of lactones with ketene silyl acetals gives simple Mukaiyama aldol adducts in excellent yields. In contrast, the same reaction in the presence of a carbon acid catalyst brings about the formation of olefination products in a Z‐selective manner.

1,2,3,4-Tetrasubstituted naphthalenes bearing four different substituents were synthesized in a regioselective manner through a fluoride-induced cascade reaction of lactol silyl ethers, which could be easily prepared from 4-alkynylisocoumarins and ketene silyl acetal.

4-Aryl-1,3-dihydroxy-2-naphthoates having the less accessible 1,2,3,4-tetrasubstituted naphthalene scaffold and that show photoluminescence emission from solid state as well as in solutions, were selectively synthesized from brominated lactol silyl ethers through the 1,2-aryl-migrative ring rearrangement reaction.

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