Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements.
Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent with the [3,3]-sigmatropic rearrangement mechanism, while those of branched allyl ethers provided [3,3]- and [1,3]-rearrangement products through the formation of a tight ion-dipole pair.
Department of Chemistry and Institute for Natural Sciences, Hanyang University, Seoul, 133-791, Korea.
Jungho
J
Jun
Hyu-Suk
HS
Yeom
Jun-Hyun
JH
An
Seunghoon
S
Shin
[1,3]-rearrangement; [3,3]-sigmatropic rearrangement; gold catalysis; intermolecular coupling; sulfonylacetylene