Iodoarene catalysts can be applied in versatile reactions, for instance in the construction of complex chiral molecules via dearomatization of simple aromatic compounds. Recently, we reported the synthesis of the first carbohydrate-based chiral iodoarene catalysts and their application in asymmetric catalysis. Here we describe the synthesis of some new and improved catalysts. An account on how we got to the improved catalyst design, as well as the X-ray structure of one of the carbohydrate-based iodoarenes, is given.
Keywords: Mitsunobu reaction; asymmetric catalysis; benzylic substitution; bulky substituent; carbohydrate; dearomatization; iodoarene; organocatalysis; spirolactonization.