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The photosensitized singlet oxygen addition to a silyl enol ether

✍ Scribed by George M. Rubottom; Mayda I. Lopez Nieves


Publisher
Elsevier Science
Year
1972
Tongue
French
Weight
144 KB
Volume
13
Category
Article
ISSN
0040-4039

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The EtAICl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkyttes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo-fashion to give mono-and bicyclic p,T-unsaturated ketones in good to excellent yields.

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Silyl enol ethers are currently much interested in respect to the reaction of enolate anion, and many reports have been made on the formation and spectra of these compounds. 1 Little has been known, however, about the reactivity on the @-carbon of these compounds except trimethylsilylacetals. 2 We

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## Abstract Chelate‐controlled Mukaiyama reaction of silyl enol ethers 2a, 2b, 2c, and 2d with β‐formylcarboxylate 1 in the presence of TiCl~4~ provided γ‐lactones 3a, 3b, 3c, and 3d in very good yields and with good to excellent __trans__ selectivities. The use of BF~3~, SnCl~4~, and SnBr~4~ as Le