Enantioselective Photochemistry through Lewis Acid Catalyzed Triplet Energy Transfer

Tehshik P. Yoon uses Lewis acid catalyzed triplet energy transfer to perform enantioselective photochemistry.

Carbonyl photochemistry is prominent in many of the most important reactions in photochemical synthesis. It has been known for many decades that the photochemical properties of carbonyl compounds can be modulated by Lewis acid catalysts. In the 1980s it was shown that the coordination of enones to oxophilic Lewis acids such as BF3 and EtAlCl2 could completely change the energetics of their singlet excited states. Changes to the UV absorption spectra of coordinated enones and in an increased efficiency of subsequent photocycloaddition reactions are results of this phenomenon which already led to the design of highly enantioselective photocycloaddition reactions using chiral Lewis acids. The group of Professor Tehshik P. Yoon from the University of Wisconsin–Madison (USA) has also been working in this area and the central discovery reported recently is that Lewis acids can have a similarly large impact on the triplet excited states of enones.

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