| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348851 | Tetrahedron: Asymmetry | 2005 | 9 Pages |
Oxidatively generated oxocarbenium ions are shown to be effective promoters of polyepoxide cascade cyclization reactions to form polyether compounds. The reaction conditions are neutral, ensuring that background acid-mediated processes are not operative and that other acid-sensitive functional groups, such as acetals, can be incorporated into cyclization substrates. While 5-exo pathways are more common that 6-endo pathways, a rational design has been employed to access tetrahydropyranyl ethers.
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(R)-2-Ethoxy-2-((2S,5S)-tetrahydro-5-((R)-tetrahydro-5-(octyloxy)furan-2-yl)furan-2-yl)ethanolC20H38O5[α]D25=-8.5 (c 0.30, EtOAc)Source: asymmetric synthesis
(2S,3R,4S,6R)-3-(4-(Trifluoromethyl)benzyloxy)tetrahydro-6-methoxy-2-methyl-2H-pyran-4-olC15H17F3O4[α]D25=-129.3 (c 0.18, EtOAc)Source: asymmetric synthesis
(S)-2-Ethoxy-2-((2R,5S)-tetrahydro-5-((R)-tetrahydro-5-(octyloxy)furan-2-yl)furan-2-yl)ethanolC20H38O5[α]D25=-3.8 (c −0.45, EtOAc)Source: asymmetric synthesis
