期刊
ORGANIC LETTERS
卷 18, 期 5, 页码 928-931出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03522
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资金
- National Science Foundation [CHE-1465142]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1465142] Funding Source: National Science Foundation
Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to an equilibrating mixture of oxonium ions of similar stability. This mixture is kinetically self-sorted via a highly exothermic cyclization. Selective formation of 1,2-dialkoxy naphthalenes originates from chemoselective aromatization of the cyclic intermediate via 1,4-elimination of methanol.
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