The Diels–Alder reactivity of 2-vinylindenes: synthesis of functionalized tetrahydrofluorenes
SM Wilkerson-Hill, CM Lavados, R Sarpong - Tetrahedron, 2016 - Elsevier
Functionalized tetrahydrofluorenes were synthesized using a normal electron-demand Diels–
Alder cycloaddition reaction between 2-vinylindenes and various dienophiles. Electron rich
2-vinylindenes bearing methoxy groups at the 4-and 7-positions were accessed through
their corresponding 2-indenylpivalates obtained using a Pt-catalyzed cycloisomerization
reaction. DFT calculations were used to rationalize the observed regioselectivity in the Diels–
Alder reaction, and the cycloadditions were extended to a 2-allenylindene substrate.
Alder cycloaddition reaction between 2-vinylindenes and various dienophiles. Electron rich
2-vinylindenes bearing methoxy groups at the 4-and 7-positions were accessed through
their corresponding 2-indenylpivalates obtained using a Pt-catalyzed cycloisomerization
reaction. DFT calculations were used to rationalize the observed regioselectivity in the Diels–
Alder reaction, and the cycloadditions were extended to a 2-allenylindene substrate.
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