Tetrahedron Letters p. 4197 - 4200 (1993)
Update date:2022-08-04
Topics:
Duhamel
Guillemont
Poirier
Chabardes
Depending on the steric hindrance of the reaction centers, hemiacetal vinylogs 1 in the presence of BF3.OEt2 can, with enol ethers, lead to a Michael-type addition (4) or an aldolisation-type reaction (3). Hemiacetal vinylog 1b always yields the second reaction leading to β-methoxy-γ,δ-ethylenic carbonyl compounds 4 precursors of polyenic carbonyl compounds 5. Crotonaldehyde and methanol can be used instead of compound 1b.
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Doi:10.1016/S0040-4039(01)80435-4
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