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- Title
Gold-Catalyzed Sequential Cyclization of 1-En-3,9-Diyne Esters to Partially Hydrogenated 3 H-Dicyclopenta[ a, b]naphthalenes.
- Authors
Rao, Weidong; Boyle, Joshua William; Chan, Philip Wai Hong
- Abstract
A synthetic method that relies on a gold(I)-catalyzed cycloisomerization of 1-en-3,9-diyne esters to spiro[4.4]non-2-ene-substituted 1,2-dihydronaphthalenes is described. Robust with a wide variety of substitution patterns tolerated, the reaction provides the first example of a one-step strategy to construct such novel and architecturally challenging members of the carbocycle family in good to excellent yields. A mechanism is proposed in which the sequential cycloisomerization pathway was thought to involve a gold-catalyzed 1,3-acyloxy migration/Nazarov cyclization followed by a formal [4+2] cycloaddition to give the tetracarbocyclic product.
- Subjects
NAPHTHALENE synthesis; GOLD catalysts; RING formation (Chemistry); HYDROGENATION; CYCLOISOMERIZATION
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 19, p6532
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201600915