Sunlight-Promoted CO2 Transformations: Synthesis of α-Amino Acids with Imines

Xinyuan Fan and Patrick Walsh present the synthesis of α-amino acids by sunlight-promoted CO2 Transformations.

The importance of α-amino acids is broadly documented in synthesis, catalysis, protein science and biomedical research. Efficient chemical synthesis of α-amino acids has long been a pursuit of organic chemists. CO2 is a nontoxic, abundant and renewable C1 synthon that is an ideal carboxyl source for the synthesis of α-amino acids. Due to its relatively inert nature, however, very strong nucleophilic reagents such as RMgX or RLi are usually required to attack CO2 to form C–C bonds. Professor Xinyuan Fan (Nanjing Tech University, P. R. of China), Professor Patrick Walsh (University of Pennsylvania, USA, Honorary Professor at Nanjing Tech University, P. R. of China) and their co-workers previously demonstrated that benzophenone ketimines, which are conventionally electrophilic, exhibit umpolung reactivity under photoredox catalytic conditions. Thus, in the presence of a sacrificial amine, photoredox catalyst and visible light, these ketimines were found to undergo single-electron reduction and H· abstraction to generate carbon-centered carbanions.


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