Synthesis of Pyrrolidines and Pyrrolidinones by the Rhodium Complex Catalyzed Cyclization of Unsaturated Amines

Article abstract of DOI:10.1021/jo00038a019

N-Allylic arylamines react with carbon monoxide, sodium borohydride, 2-propanol, and catalytic amounts of the zwitterionic complex η⁶-C6H6BPh3^-Rh(COD)⁺ (1), to form pyrrolidines as the main products in most cases.Pyrrolidinones result from N-allylic alkylamines.An alternate route to the lactams from N-allylic alkylamines involves synthesis gas instead of CO/NaBH4, together with the dual catalytic system 1/2.Complementary to the N-allylic arylamine route to pyrrolidines with NaBH4 and 1 is the use of synthesis gas, 1, and 1,4-bis(diphenylphosphino)butane.