Enantioselective Cobalt(III)-Catalyzed [4 + 1] Annulation of Benzamides: Cyclopropenes as One-Carbon Synthons
A chiral cyclopentadienyl cobalt(III)-catalyzed enantioselective [4 + 1] annulation of <i>N</i>-chlorobenzamides with cyclopropenes is reported. The cobalt catalyst engages in the C–H activation as well as promotes the C–C bond cleavage of the cyclopropene, rendering it as a one-carbon u...
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2025
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| Summary: | A chiral cyclopentadienyl cobalt(III)-catalyzed enantioselective [4 + 1] annulation of <i>N</i>-chlorobenzamides with cyclopropenes is reported. The cobalt catalyst engages in the C–H activation as well as promotes the C–C bond cleavage of the cyclopropene, rendering it as a one-carbon unit for the annulation. The reaction efficiently constructs biologically relevant chiral isoindolinones with selectivities of up to 99:1 er and >20:1 <i>E</i>/<i>Z</i> ratios. The cobalt(III) catalyst displays a unique orthogonal reactivity profile delivering [4 + 1] annulation products, whereas its rhodium(III) homologue engages in the more classical [4 + 2] annulation pattern. Computational studies reveal the origin of these reactivity divergences. |
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