477961-07-2Relevant academic research and scientific papers
Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones
Price, Michael D.,Kurth, Mark J.,Schore, Neil E.
, p. 7769 - 7773 (2007/10/03)
Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, Cα-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the Cα-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.
