The synthesis of (RS)-2- or (RS)-3-methoxy-2,3-dihydro-5H-1,4-benzodioxepins and (RS)-5- or (RS)-3-methoxy-2,3,5,6-tetrahydro-8H-benzo-[1,4,7]-trioxecins has been developed. The mechanism of such a reaction via the boron trifluoride etherate-promoted transformation of 2-(methoxyethoxymethoxy)benzyloxyacetaldehyde dimethyl acetals or 2-(methoxyethoxymethoxymethyl)phenyloxyacetaldehyde dimethyl acetals has been proposed. Transannular versions of the reaction results in the facile ring contraction of 12-membered intermediates to the 10- and to 7-membered benzene-fused O,O-acetals. The characterization of the by-products strongly supports the mechanisms proposed.
|Numero di pagine||12|
|Stato di pubblicazione||Published - 2004|
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry
Aiello, S., Díaz-Gavilán, M., Gallo, M. Á., Saniger, E., Choquesillo, D., González-Pérez, J. M., Espinosa, A., Aiello, S., Campos, J. M., & Delgado, B. (2004). Substituent effects on the reaction mode between 2-hydroxybenzyl alcohol derivatives and MEM chloride:synthesis and mechanistic aspects of seven-and ten-membered benzo-fused O,O-acetals. Tetrahedron, 60, 11453-11464.