American Chemical Society
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Zn-ProPhenol Catalyzed Enantioselective Mannich Reaction of 2H‑Azirines with Alkynyl Ketones

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journal contribution
posted 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.