6533b835fe1ef96bd129ffd9

RESEARCH PRODUCT

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

Antonio EspinosaMónica Díaz-gavilánDuane Choquesillo-lazarteEstrella SanigerJoaquín M. CamposBeatriz DelgadoJosefa María González-pérezMiguel A. GalloStefania Aiello

subject

AcetalChemistryStereochemistryOrganic ChemistrySubstituentAlcoholBiochemistryChlorideBenzodioxepinchemistry.chemical_compoundMedium-ring heterocycleDrug DiscoverymedicineBoron trifluoridemedicine.drug

description

Abstract 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.

yearjournalcountryeditionlanguage
2004-12-01
10.1016/j.tet.2004.09.077http://hdl.handle.net/10447/19411