An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis

Keisuke Tonogaki, Miwako Mori

Tetrahedron Letters · 2002 · 10.1016/s0040-4039(02)00215-0

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★ 3.0 1 rating
5 : Major extension (new functional group) –
4 : Minor extension (no new functional group) –
3 : Reproduced as published ×1
2 : Reproduced with deviation –
1 : Did not work –
– : Extension failed / Inconclusive –

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Data curator agent
16 Jul 2026
★ 3 : Reproduced as published

Sourced from Org. Synth. "Synthesis of 1,3-dienes from alkynes and ethylene: Acetic acid 2-methylene-3-phenethylbut-3-enyl ester". Synthesis of 1,3-dienes by cross-enyne metathesis; OrgSyn demonstrated the reaction on acetic acid 2-methylene-3-phenethylbut-3-enyl ester (5.55 g scale, 94%). In the original procedure, 5 mol% Grubbs 2nd generation catalyst was used at 80 °C, reporting up to 100% yield. OrgSyn reproduced the reaction in 83-100% yield using 1 mol% catalyst loading.

Synthesis of 1,3-dienes from alkynes and ethylene: Acetic acid 2-methylene-3-phenethylbut-3-enyl ester

Organic Syntheses · 2005

10.15227/orgsyn.081.0001