Abstract
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.
Highlights
IntroductionCarbohydrates contain a large amount of stereochemical information
Carbohydrates can be isolated from many different sources; common carbohydrates like d-glucose, d-galactose, or d-fructose are commercially available at low cost [1]
Our first attempt to improve the enantioselectivity of our carbohydrate-based iodoarene catalysts was to change the linkage between the monosaccharide and the iodine-substituted aromatic ring
Summary
Carbohydrates contain a large amount of stereochemical information. They have already been widely used as starting materials for chiral auxiliaries as well as for the synthesis of chiral ligands for enantioselective, transition metal catalyzed reactions [2,3,4,5,6,7]. Transition metal catalyzed reactions provide a plethora of selective chemical modifications with a high tolerance against many functional groups [8]. Metal-catalyzed reactions were nearly the only way of performing enantioselective catalytic reactions in an effective way. Advantages of organocatalysis over transition metal catalysis are, for example, their lower toxicity and lower cost of the catalysts. Organocatalysts are often more tolerant against moisture and oxygen [10]
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