An indium-mediated allylative/transesterification DFT-directed approach to chiral C(3)-functionalized phthalides

Article abstract of DOI:10.1021/ol301566f

A one-pot synthesis of chiral C₍₃₎-substituted phthalides via an indium-mediated allylation/transesterification reaction is described. The development of this reaction was facilitated through the applied use of DFT calculations to rationalize the stereoselection of a chiral In-mediated process. It was discovered that the enantiomeric excess of this reaction depended upon the steric size, chain length, and substitution of the aldehyde employed.