An indium-mediated allylative/transesterification DFT-directed approach to chiral C(3)-functionalized phthalides.
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.
Department of Chemistry, Brock University , 500 Glenridge Avenue, St. Catharines, Ontario, Canada L2S 3A1.
Roya
R
Mirabdolbaghi
Travis
T
Dudding
D000447:Aldehydes / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004951:Esterification; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
D000447:Aldehydes; D001572:Benzofurans; D007204:Indium; C082022:phthalide