Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones

Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, C_α-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the C_α-allylation and iodolactonization processes indicate that incorporation of a non-C₂-symmetric auxiliary as a polymer cross-link gives results superior to those obtained either in solution or with other non-C₂-symmetric auxiliaries and comparable to those observed using a polymer-supported pseudo-C₂-symmetric auxiliary.