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Synthesis of (Z)-Cinnamate Esters by Nickel-Catalyzed Stereoinvertive Deoxygenation of trans-3-Arylglycidates

Sunisa Akkarasamiyo*, Saranya Chitsomkhuan, Supawadee Buakaew, Joseph S. M. Samec, Pitak Chuawong, Punlop Kuntiyong

*Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok, 10900, Thailand, Email:

S. Akkarasamiyo, S. Chitsomkhuan, S. Buakaew, J. S. M. Samec, P. Chuawong, P. Kuntiyong, Synlett, 2022, 33, 1353-1356.

DOI: 10.1055/s-0040-1719911

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A stereoinvertive deoxygenation of trans-3-arylglycidates provides thermodynamically less stable (Z)-cinnamate esters by using nickel triflate and triphenylphosphine. The reaction offers broad functional group tolerance and affords the corresponding (Z)-cinnamate esters in high yields and with moderate to high E/Z ratios.

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Key Words

alkenes, unsaturated esters, nickel catalysis, triphenylphosphine

ID: J72-Y2022