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Zn-ProPhenol Catalyzed Enantioselective Mannich Reaction of 2H‑Azirines with Alkynyl Ketones
journal contributionposted on 2020-12-03, 12:33 authored by Barry M. Trost, Chuanle Zhu
The enantioselective Mannich reaction of 2H-azirines with alkynyl ketones is achieved under Zn-ProPhenol catalysis, delivering various aziridines with vicinal tetrasubstituted stereocenters in high yields with excellent enantioselectivities. The bimetallic Zn-ProPhenol complexes activate both the nucleophile and the electrophile in the same chiral pocket. A unique intramolecular hydrogen bond is observed in the obtained Mannich adducts, which lowers the basicity of the product’s aziridine nitrogen thus favoring enantioselective control and allowing catalyst turnover.
chiral pocketintramolecular hydrogen bondcatalyst turnoveralkynyl ketonesAlkynyl Ketonesenantioselective controlZn-ProPhenol Catalyzed Enantioselec...vicinal tetrasubstituted stereocentersZn-ProPhenol catalysisenantioselective Mannich reaction2 HMannich adductsaziridinebimetallic Zn-ProPhenol complexes