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

doi:10.1055/s-0040-1719911

Synlett, Table of Contents

Synlett 2022; 33(14): 1353-1356
DOI: 10.1055/s-0040-1719911

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Organic Chemistry in Thailand

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

Sunisa Akkarasamiyo∗

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok, 10900, Thailand

,

Saranya Chitsomkhuan

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok, 10900, Thailand

,

Supawadee Buakaew

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok, 10900, Thailand

,

Joseph S. M. Samec

^bDepartment of Organic Chemistry, Stockholm University, 106 91 Stockholm, Sweden

,

Pitak Chuawong

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok, 10900, Thailand

,

Punlop Kuntiyong

^cDepartment of Chemistry, Faculty of Science, Silpakorn University, Sanamchandra Palace Campus, Nakhon Pathom, 73000, Thailand

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Abstract

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Abstract

We report a stereoinvertive deoxygenation of trans-3-arylglycidates as an alternative route to access thermodynamically less stable (Z)-cinnamate esters by using nickel triflate and triphenylphosphine. Broad functional-group tolerance was observed, with trans-3-arylglycidates containing methyl, methoxy, halo, or nitro groups affording the corresponding (Z)-cinnamate esters in high yields and with moderate to high E/Z ratios.

Key words

deoxygenation - epoxides - cinnamate esters - nickel catalysis

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References and Notes

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16 (Z)-Cinnamates 2a–l; General Procedure A dried tube was charged with Ni(OTf)₂ (5 mol%) and PPh₃ (2 equiv), then capped and flushed with argon. A solution of trans-3-arylglycidates 1 (1 mmol) in toluene (4 mL) was added and the mixture was stirred at 80 °C for 18 h. The solvent was evaporated under reduced pressure and the mixture was then purified by column chromatography (silica gel, hexane then EtOAc–hexane gradient). Methyl (Z)-Cinnamate (2a) Colorless oil; yield: 114 mg (70%). ¹H NMR (400 MHz, CDCl₃): δ = 7.65–7.57 (m, 2 H), 7.44–7.31 (m, 3 H), 6.96 (d, J = 12.6 Hz, 1 H), 5.97 (d, J = 12.6 Hz, 1 H), 3.72 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 166.6, 143.4, 134.8, 129.8 (2 C), 129.1, 128.1 (2 C), 119.3, 51.4. HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₀H₁₀NaO₂: 185.0573; found: 185.0573

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