Work

Cobalt-Catalyzed Enantioselective Intermolecular C–H Carboamination with Racemic Allenes

Year: 2026

Type: article

Abstract: Enantioselective carboamination of allenes especially in conjunction with 3D-metal catalysis remains a significant challenge. We report chiral cyclopentadienyl cobaltIII-catalyzed regio-, chemo-, and enantioselective intermolecular C–H carboamination of racemic allenyl esters with N-phenoxyisobutyramides. The protocol offers an efficient approach for highly selective carboamination of allenes and affords synthetically valuable chiral γ-substituted-β-enamido esters with exceptional selectivities (up to 88% yield, >99:1 er, and >20:1 E/Z). Operating by a kinetic resolution pathway, the transformation was additionally optimized for recovery of enantioenriched allenes with high selectivity factors of up to 138. The utility was showcased by the resolution of methyl-(R,E)-(−)-tetradeca-2,4,5-trienoate, the male bean weevil pheromone.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6c14940

Authors: Lenin Kumar Verdhi, Nicolai Cramer

Institution: École Polytechnique Fédérale de Lausanne

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, École Polytechnique Fédérale de Lausanne, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung