Experimental study demonstrates asymmetric copper-catalyzed addition yielding vicinal fluorinated stereocenters with high stereocontrol, highlighting versatile pathways for organofluorine synthesis.
Herein, we report a copper-catalyzed asymmetric Michael addition of α-fluoro aza-heteroarenyl acetates to β-fluoroalkyl enones. This transformation provides efficient access to enantioenriched acyclic vicinal F/CFx-containing (vicinal F and CF3, F and CHF2, F and CH2F) stereocenters with exceptional stereocontrol (up to >20:1 dr and 98% ee). Its synthetic utility is underscored by scale-up synthesis and diverse downstream functionalizations. Detailed mechanistic investigations and density functional theory calculations elucidate the catalytic cycle process and the origin of enantioselectivity.
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Yang et al. (2026) studied this question.
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