The enantioselective Mannich reaction of 2-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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| http://dx.doi.org/10.1021/acs.orglett.0c03737 | DOI Listing |
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