3 years ago

Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid

Enantioselective Synthesis of Tetrahydroquinolines by Borrowing Hydrogen Methodology: Cooperative Catalysis by an Achiral Iridacycle and a Chiral Phosphoric Acid
Ching Si Lim, Thanh Truong Quach, Yu Zhao
We report herein the highly enantioselective synthesis of 2-substituted tetrahydroquinolines through borrowing hydrogen, a process recognized for its environmentally benign and atom-economical nature. The use of an achiral iridacycle complex in combination with a chiral phosphoric acid as catalysts was the key to the development of this highly efficient and enantioselective transformation. Waste not, want not: A highly enantioselective synthesis of tetrahydroquinolines was made possible by hydrogen-borrowing methodology under the cooperative catalysis of an achiral iridacycle and a chiral phosphoric acid (see scheme). This redox-neutral process without any stoichiometric reagent is a practical example of an environmentally benign transformation with high atom economy.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703704

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