A rationally designed chiral auxiliary for hydroxyalkyl radicals leads to exceptional ρ-stereocontrol

Article abstract of DOI:10.1016/S0040-4039(97)01580-3

Substitution of a t-butyl group at C-6 of the THP ring results in a chiral auxiliary that exerts exceptional stereocontrol in radical addition reactions. For example, radical 2c adds to 2-nitropropene at -78°C to give, after reductive hydrolysis, the prot