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Catalytic Enantioselective Hetero-dimerization of Acrylates and 1,3-Dienes

Stanley M. Jing , Vagulejan Balasanthiran , Vinayak Pagar, Judith C. Gallucci and T. V. RajanBabu*

*Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States, Email: rajanbabu.1osu.edu

S. M. Jing, V. Balasanthiran, V. Pagar, J. C. Gallucci, T. V. Rajanbabu, J. Am. Chem. Soc., 2017, 139, 18034-18043.

DOI: 10.1021/jacs.7b10055 (free Supporting Information)


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Abstract

A practical, highly enantioselective reaction of readily available 1,3-dienes and alkyl acrylates provides valuable, enantio-pure skipped 1,4-diene esters in the presence of commercially available cobalt salts and chiral ligands. This hetero-dimerization reaction tolerates various organic functional groups (e.g., aromatic substituents, halides, isolated mono- and di-substituted double bonds, esters, silyl ethers, and silyl enol ethers).

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proposed mechanism



Key Words

1,4-dienes, α,β-unsaturated compounds


ID: J48-Y2017