ROLE OF STERIC, ELECTROSTATIC AND HYDROGEN BONDING EFFECTS AS FACE SELECTIVITY CONTROLLING FACTORS IN NITRONE CYCLOADDITIONS

Article abstract of DOI:10.1016/S0040-4039(00)95332-2

A highly selective syn-attack is promoted by hydrogen bonding effects in the reaction of nitrones with endo-5-hydroxybicyclo<2.2.2>oct-2-enes.By contrast repulsive interactions ( steric and electrostatic) between other kinds of substituents and the attacking nitrone result in an almost exclusive anti selectivity.