Ireland-Claisen rearrangements on chiral acids

CHED 599

Amanda Doty, ad151737@rc.hsu.edu and Martin J. Campbell, campbem@hsu.edu. Department of Chemistry, Henderson State University, 1100 Henderson St., Arkadelphia, AR 71999
A series of esters prepared from appropriately substituted allyl alcohols and á-chiral carboxylic acids was prepared and subject to Ireland-Claisen rearrangement. The allyl alcohols had various C-3 substitution patterns that after rearrangement led to 4-pentenoic acids having vicinal quaternary stereocenters. An attempt was made to correlate the size of the alcohol substituents with possible transition states leading to observed stereochemistry.