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Zn-ProPhenol Catalyzed Enantioselective Mannich Reaction of 2H‑Azirines with Alkynyl Ketones
journal contribution
posted on 2020-12-03, 12:33 authored by Barry M. Trost, Chuanle ZhuThe
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.
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Keywords
chiral pocketintramolecular hydrogen bondcatalyst turnoveralkynyl ketonesAlkynyl Ketonesenantioselective controlZn-ProPhenol Catalyzed Enantioselec...vicinal tetrasubstituted stereocentersZn-ProPhenol catalysisenantioselective Mannich reaction2 HMannich adductsaziridinebimetallic Zn-ProPhenol complexes