Asymmetric epoxidation of chromenes catalyzed by chiral pyrrolidine SalenMn(III) complexes with an anchored functional group

• Chiral pyrrolidine SalenMn(III) complexes with an anchored functional group at the N-aza-substituent in the pyrrolidine backbone were synthesized, and used as catalysts for asymmetric epoxidation of substituted chromenes. The complex 1 with an anchored imidazole as acceptor could effectively catalyze epoxidation of substituted chromenes in the absence of expensive additive 4-phenyl pyridine N-oxide (PPNO) by the coordination of the anchored organic base to the central manganese ion. Complexes 2 and 3 with a quaternary ammonium salt unit at the Naza-substituent in the pyrrolidine backbone displayed higher activities than Jacobsen catalyst and the analogous complex 4 without anchored functional group in the aforementioned reaction.

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