Intramolecular addition of vinyl radicals to aldehydes

DOI: 10.1016/S0040-4039(97)10743-2

Source and publish data:

Tetrahedron Letters p. 833 - 836 (1998)

Update date:2022-07-29

Topics:

Authors:

Devin, Priscille

Fensterbank, Louis

Malacria, Max

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Article abstract of DOI:10.1016/S0040-4039(97)10743-2

The reaction of aldehydes 1 and 10 with Bu₃SnH has been studied. In thermal conditions, after an initial chemoselective 6-exo-trig or 5-exo-trig cyclization to the aldehyde, a β-scission reaction takes place, providing rearrangement products. At low temperature, using the Et₃B/O₂ procedure, satisfactory yields of cyclohexanol 2 and cyclopentanol 11 are obtained.

Full text of DOI:10.1016/S0040-4039(97)10743-2

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