Iridium-Catalyzed Enantioselective Direct α-C–H Alkylation of Saturated Cyclic Amines with Alkenes
Daisuke Yamauchi, Kentaro Yamakawa, Takahiro Nishimura
Abstract
Enantioselective direct α-C(sp3)–H alkylation of saturated cyclic amines having N-methylbenzimidazolyl as a directing group was realized by using a cationic iridium/chiral diphosphine catalyst. The alkylation of pyrrolidine derivatives with various terminal alkenes proceeded to give α-alkylated products in high yields with high enantioselectivities. Chiral α,α′-dialkylated pyrrolidine derivatives were also synthesized by using an excess of alkenes or by stepwise alkylation.
Topics & Concepts
AlkylationChemistryPyrrolidineEnantioselective synthesisIridiumCatalysisCationic polymerizationOrganic chemistryMedicinal chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis