Is a hydrogen bonded carbene an intermediate in the organoaluminum-induced ring opening of pyranosides?
Semiempirical and ab initio quantum chemical computations indicate that the intermediate formed prior to the selectivity-determining methyl transfer step in the reaction between glycosides and trimethylaluminum is a strongly hydrogen-bended equilibrium OH...C = O-H...C, which is proposed to be an important selectivity promoting factor in the alkyl transfer reaction.